Synthesis of 3-Iodoquinolines by Copper-Catalyzed Tandem Annulation from Diaryliodoniums, Nitriles, and 1-Iodoalkynes

A novel method for the synthesis of 3‐iodoquinolines was developed by copper‐catalyzed tandem annulation from diaryliodoniums, nitriles, and 1‐iodoalkynes. It is a method that is characterized by the most convenient operation and wide molecular diversity.

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Published in	Advanced synthesis & catalysis Vol. 358; no. 14; pp. 2332 - 2339
Main Authors	Wang, Xuesong, Wang, Xingyong, Huang, Dayun, Liu, Chulong, Wang, Xinyan, Hu, Yuefei
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 14.07.2016 WILEY‐VCH Verlag Wiley
Subjects	1-iodoalkynes annulation Catalysis Chemical reactions Chemistry Chemistry, Applied Chemistry, Organic copper catalysts iodoniums Nitriles Organic chemistry Physical Sciences Science & Technology Synthesis synthesis of quinolones tandem reactions ELECTROPHILIC CYCLIZATION PALLADIUM 1-iodoalkynes iodoniums ONE-POT SYNTHESIS synthesis of quinolones 3-HALOQUINOLINES ORGANIC AZIDES ALKYNES annulation REGIOSELECTIVE SYNTHESIS OPTIMIZATION copper catalysts DERIVATIVES tandem reactions SUBSTITUTED QUINOLINES
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Abstract	A novel method for the synthesis of 3‐iodoquinolines was developed by copper‐catalyzed tandem annulation from diaryliodoniums, nitriles, and 1‐iodoalkynes. It is a method that is characterized by the most convenient operation and wide molecular diversity.
AbstractList	A novel method for the synthesis of 3-iodoquinolines was developed by copper-catalyzed tandem annulation from diaryliodoniums, nitriles, and 1-iodoalkynes. It is a method that is characterized by the most convenient operation and wide molecular diversity. A novel method for the synthesis of 3‐iodoquinolines was developed by copper‐catalyzed tandem annulation from diaryliodoniums, nitriles, and 1‐iodoalkynes. It is a method that is characterized by the most convenient operation and wide molecular diversity. magnified image
Author	Liu, Chulong Wang, Xingyong Hu, Yuefei Huang, Dayun Wang, Xuesong Wang, Xinyan
Author_xml	– sequence: 1 givenname: Xuesong surname: Wang fullname: Wang, Xuesong organization: Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Fax: (+86)-10-6277-1149; phone: (+86)-10-6279-5380 – sequence: 2 givenname: Xingyong surname: Wang fullname: Wang, Xingyong organization: Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Fax: (+86)-10-6277-1149; phone: (+86)-10-6279-5380 – sequence: 3 givenname: Dayun surname: Huang fullname: Huang, Dayun organization: Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Fax: (+86)-10-6277-1149; phone: (+86)-10-6279-5380 – sequence: 4 givenname: Chulong surname: Liu fullname: Liu, Chulong organization: Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Fax: (+86)-10-6277-1149; phone: (+86)-10-6279-5380 – sequence: 5 givenname: Xinyan surname: Wang fullname: Wang, Xinyan email: wangxinyan@mail.tsinghua.edu.cn organization: Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Fax: (+86)-10-6277-1149; phone: (+86)-10-6279-5380 – sequence: 6 givenname: Yuefei surname: Hu fullname: Hu, Yuefei email: yfh@mail.tsinghua.edu.cn organization: Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Fax: (+86)-10-6277-1149; phone: (+86)-10-6279-5380
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Cites_doi	10.1246/cl.2007.1422 10.1021/cr60111a001 10.1016/j.jfluchem.2011.08.005 10.1021/ja1045378 10.1055/s-0030-1259097 10.1016/j.ejmech.2015.02.002 10.1021/jm500147k 10.1021/jm200718m 10.1016/j.tet.2007.06.011 10.1016/j.ccr.2007.06.003 10.1021/jm8013629 10.1002/asia.200900018 10.1039/C5RA07798B 10.1039/c0gc00342e 10.1016/j.ejmech.2013.09.044 10.1002/1521-3773(20020816)41:16<2991::AID-ANIE2991>3.0.CO;2-6 10.1021/jo9600215 10.1021/jo2008252 10.1021/jo901101v 10.1021/jo902603v 10.1021/jo300841c 10.1039/c4gc00451e 10.1021/jm400694d 10.1021/ol2007154 10.1021/cs500326e 10.1021/ol0476218 10.1021/jm500372e 10.1080/02603594.2014.959116 10.1126/science.1169975 10.1016/j.tet.2009.12.012 10.1002/1521-3757(20020816)114:16<3117::AID-ANGE3117>3.0.CO;2-U 10.1016/j.bmcl.2014.03.056 10.1016/j.tet.2011.04.040 10.1016/j.tet.2013.08.019 10.1002/ejic.201200789 10.1021/jm400282d 10.1002/ejoc.201500461 10.1002/anie.200903558 10.1021/ja405972h 10.1039/C4RA01814A 10.1016/j.jfluchem.2013.10.006 10.1039/c1cc12694f 10.1016/j.biopha.2014.10.007 10.1016/j.tet.2010.06.018 10.1021/ol052518j 10.1039/B815398A 10.1002/ange.200903558 10.1016/j.tet.2010.08.043 10.1021/cr800482c 10.1021/acs.joc.5b00375 10.1002/chem.201402559 10.1021/ja201425e 10.1055/s-2003-40531 10.1016/S0040-4039(02)01240-6 10.1016/j.ejmech.2011.02.034 10.1021/ol502654a 10.1016/j.ccr.2011.01.013 10.1021/ol060538v 10.1039/c2ra20213a 10.1016/j.drudis.2012.11.003 10.1021/jo502634h 10.1021/ja901414u 10.5012/bkcs.2004.25.7.1091 10.1126/science.1229506 10.1002/anie.201300586 10.1038/nature11008 10.1039/C4RA15980B 10.1002/ange.201303724 10.1021/ol201290q 10.2174/138527208785740300 10.1021/jo1011174 10.1002/ange.201300586 10.1039/C4CC08363F 10.1021/cr60134a002 10.1016/S0040-4020(98)00374-3 10.1002/anie.201303724 10.1021/acs.orglett.5b01860 10.1016/j.jorganchem.2014.06.008 10.1016/j.tetlet.2013.01.018 10.1016/j.ejmech.2014.07.044 10.1039/b815398a 10.1055/s-2005-921919 10.1039/c4ra15980b 10.1039/c4ra01814a 10.1039/c4cc08363f 10.1021/ja3039807 10.1039/c5ra07798b
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Keywords	ELECTROPHILIC CYCLIZATION PALLADIUM 1-iodoalkynes iodoniums ONE-POT SYNTHESIS synthesis of quinolones 3-HALOQUINOLINES ORGANIC AZIDES ALKYNES annulation REGIOSELECTIVE SYNTHESIS OPTIMIZATION copper catalysts DERIVATIVES tandem reactions SUBSTITUTED QUINOLINES
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References	J. S. Oakdale, R. K. Sit, V. V. Fokin, Chem. Eur. J. 2014, 20, 11101-11110. S. V. Ryabukhin, V. S. Naumchik, A. S. Plaskon, O. O. Grygorenko, A. A. Tolmachev, J. Org. Chem. 2011, 76, 5774-5781 Z. Huo, I. D. Gridnev, Y. Yamamoto, J. Org. Chem. 2010, 75, 1266-1270 J. E. Hein, J. C. Tripp, L. B. Krasnova, K. B. Sharpless, V. V. Fokin, Angew. Chem. 2009, 121, 8162-8165 A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068-12073 X. Zhang, M. A. Campo, T. Yao, R. C. Larock, Org. Lett. 2005, 7, 763-766 P. J. Campos, C.-Q. Tan, M. A. Rodriguez, E. Anon, J. Org. Chem. 1996, 61, 7195-7197. R. H. Reitsema, Chem. Rev. 1948, 43, 47-68 M. Juríček, K. Stout, P. H. Kouwer, A. E. Rowan, Org. Lett. 2011, 13, 3494-3497 S. Mukherjee, M. Pal, Drug Discovery Today 2013, 18, 389-398. J. Marco-Contelles, E. Perez-Mayoral, A. Samadi, M. C. Carreiras, E. Soriano, Chem. Rev. 2009, 109, 2652-2671 U. Balijapalli, S. K. Iyer, Eur. J. Org. Chem. 2015, 5089-5098 B. H. M. Kuijpers, G. C. T. Dijkmans, S. Groothuys, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Synlett 2005, 3059-3062. R. A. Jones, S. S. Panda, C. D. Hall, Eur. J. Med. Chem. 2015, 97, 335-355 Angew. Chem. Int. Ed. 2013, 52, 5323-5327 Á. Sinai, D. Vangel, T. Gáti, P. Bombicz, Z. Novák, Org. Lett. 2015, 17, 4136-4139 G. N. Lipunova, E. V. Nosova, V. N. Charushin, O. N. Chupakhin, Comment Inorg. Chem. 2014, 34, 142-177 Y. Wang, C. Chen, J. Peng, M. Li, Angew. Chem. 2013, 125, 5431-5435 C.-C. Cheng, S.-J. Yan, Org. React. 1982, 28, 37-201 M. S. Reddy, N. Thirupathi, Y. K. Kumar, RSC Adv. 2012, 2, 3986-3992 Angew. Chem. Int. Ed. 2013, 52, 9284-9288 J. Zhang, W. Chen, B. Wang, Z. Zhao, X. Wang, Y. Hu, RSC Adv. 2015, 5, 14561-14566 R. J. Phipps, L. McMurray, S. Ritter, H. A. Duong, M. J. Gaunt, J. Am. Chem. Soc. 2012, 134, 1073-10776. O. Afzal, S. Kumar, M. R. Haider, M. R. Ali, R. Kumar, M. Jaggi, S. Bawa, Eur. J. Med. Chem. 2015, 97, 871-910 J. Barluenga, F. Rodriguez, F. J. Fananas, Chem. Asian J. 2009, 4, 1036-1048 M. J. Mphahlele, L. G. Lesenyeho, H. R. Makelane, Tetrahedron 2010, 66, 6040-6046 M. J. Mphahlele, Tetrahedron 2010, 66, 8261-8266. S. Lal, H. S. Rzepa, S. Díez-González, ACS Catal. 2014, 4, 2274-2287 A.-M. Lord, M. F. Mahon, M. D. Lloyd, M. D. Threadgill, J. Med. Chem. 2009, 52, 868-877 L. N. Tumey, D. H. Boschelli, N. Bhagirath, J. Shim, E. A. Murphy, D. Goodwin, E. M. Bennett, M. Wang, L.-L. Lin, B. Press, M. Shen, R. K. Frisbie, P. Morgan, S. Mohan, J. Shin, V. R. Rao, Bioorg. Med. Chem. Lett. 2014, 24, 2066-2072 Angew. Chem. Int. Ed. 2009, 48, 8018-8021. B. Chen, X.-L. Hou, Y.-X. Li, Y.-D. Wu, J. Am. Chem. Soc. 2011, 133, 7668-7671 B. P. Fors, N. R. Davis, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 5766-5768 C. Vidal, J. Darcía-Álvarez, Green Chem. 2014, 16, 3515-3521 J. Chen, C. Chen, J. Chen, G. Wang, H. Qu, Chem. Commun. 2015, 51, 1356-1359 H. Huang, H. Jiang, K. Chen, H. Liu, J. Org. Chem. 2009, 74, 5476-5480 D. Fu, J. Zhang, S. Cao, J. Fluorine Chem. 2013, 156, 170-176 A. P. Gorka, A. de Dios, P. D. Roepe, J. Med. Chem. 2013, 56, 5231-5246 J. S. Yadav, B. V. S. Reddy, R. S. Rao, V. Naveenkumar, K, Nagaiah, Synthesis 2003, 1610-1614 W. Chen, J. Zhang, B. Wang, Z. Zhao, X. Wang, Y. Hu, J. Org. Chem. 2015, 80, 2413-2417 F. Artizzu, M. L. Mercuri, A. Serpe, P. Deplano, Coord. Chem. Rev. 2011, 255, 2514-2529 Z. Liu, D. Zhu, B. Luo, N. Zhang, Q. Liu, Y. Hu, R. Pi, P. Huang, S. Wen, Org. Lett. 2014, 16, 5600-5603 E. K. Yum, O.-K. Yang, S. K. Kang, H. G. Cheon, S. S. Kim, J.-K. Choi, Bull. Korean Chem. Soc. 2004, 25, 1091-1094 J. García-Álverez, J. Díez, J. Gimeno, F. J. Suárez, C. Vincent, Eur. J. Inorg. Chem. 2012, 5854-5863 H. Nakamura, T. Kamakura, S. Onagi, Org. Lett. 2006, 8, 2095-2098. K. C. Majumdar, R. K. Nandi, S. Ganai, A, Taher, Synlett 2011, 116-120 R. H. F. Manske, M. Kukla, Org. React. 1953, 7, 59-72 J. Colomb, T. Billard, Tetrahedron Lett. 2013, 54, 1471-1474 E. Cahard, N. Bremeyer, M. J. Gaunt, Angew. Chem. 2013, 125, 9454-9458 J. Tummatorn, P. Poonsilp, P. Nimnual, J. Janprasit, C. Thongsornkleeb, S. Ruchirawat, J. Org. Chem. 2015, 80, 4516-4525. M. Albrecht, M. Fiege, O. Osetska, Coord. Chem. Rev. 2008, 252, 812-824. S. M. Prajapati, K. D. Patel, R. H. Vekariya, S. N. Panchal, H. D. Patel, RSC Adv. 2014, 4, 24463-24476 R. M. Cross, N. K. Namelikonda, T. S. Mutka, L. Luong, D. E. Kyle, R. Manetsch, J. Med. Chem. 2011, 54, 8321-8327 S. Bolden Jr, X. Y. Zhu, J. R. Etukala, C. Boateng, T. Mazu, H. Flores-Rozas, M. R. Jacob, S. I. Khan, L. A. Walker, S. Y. Ablordeppey, Eur. J. Med. Chem. 2013, 70, 130-142 S. Ali, H.-T. Zhu, X.-F. Xia, K.-G. Ji, Y.-F. Yang, X.-R. Song, Y.-M. Liang, Org. Lett. 2011, 13, 2598-2601 H. P. Kokatla, D. Sil, S. S. Malladi, R. Balakrishna, A. R. Hermanson, L. M. Fox, X. Wang, A. Dixit, S. A. David, J. Med. Chem. 2013, 56, 6871-6885 X. Zhang, T. Yao, M. A. Campo, R. C. Larock, Tetrahedron 2010, 66, 1177-1187 R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593-1597 A. Nilsen, G. P. Miley, I. P. Forquer, M. W. Mather, K. Katneni, Y. Li, S. Pou, A. M. Pershing, A. M. Stickles, E. Ryan, J. X. Kelly, J. S. Doggett, K. L. White, D. J. Hinrichs, R. W. Winter, S. A. Charman, L. N. Zakharov, I. Bathurst, J. N. Burrows, A. B. Vaidya, M. K. Riscoe, J. Med. Chem. 2014, 57, 3818-3834 R. I. Khusnutdinov, A. R. Bayguzina, U. M. Dzhemilev, J. Organomet. Chem. 2014, 768, 75-114 J. García-Álverez, J. Díez, J. Gimeno, Green Chem. 2010, 12, 2127-2130. X.-L. Chen, J.-M. Zhang, W.-L. Shang, B.-Q. Lu, J.-A. Jin, J. Fluorine Chem. 2012, 133, 139-145 J. A. Crossley, D. L. Browne, J. Org. Chem. 2010, 75, 5414-5416. Y. Kuninobu, Y. Inoue, K. Takai, Chem. Lett. 2007, 36, 1422-1423 A. J. Walkinshaw, W. Xu, M. G. Suero, M. J. Gaunt, J. Am. Chem. Soc. 2013, 135, 12532-12535 C. A. Boateng, X. Y. Zhu, M. R. Jacob, S. I. Khan, L. A. Walker, S. Y. Ablordeppey, Eur. J. Med. Chem. 2011, 46, 1789-1797. P. J. Campos, E. Anon, M. C. Malo, C.-Q. Tan, M. A. Rodriguez, Tetrahedron 1998, 54, 6929-6938 Angew. Chem. Int. Ed. 2002, 41, 2991-2994. A. J. Hickman, M. S. Sanford, Nature 2012, 484, 177-185 J. B. Bharate, R. A. Vishwakarma, S. B. Bharate, RSC Adv. 2015, 5, 42020-42053 B. T. Worrell, J. A. Malik, V. V. Fokin, Science 2013, 340, 457-460 S. Madapa, Z. Tusi, S. Batra, Curr. Org. Chem. 2008, 12, 1116-1183. R. S. Keri, S. A. Patil, Biomed. Pharmacother. 2014, 68, 1161-1175 W. S. Brotherton, R. J. Clark, L. Zhu, J. Org. Chem. 2012, 77, 6443-6455 H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, J. Iqbala, Tetrahedron Lett. 2002, 43, 6485-6488. K. T. J. Loones, B. U. W. Maes, R. A. Dommisse, Tetrahedron 2007, 63, 8954-8961. F. W. Bergstrom, Chem. Rev. 1944, 35, 77-277. M. J. Mphahlele, M. M. Mphahlele, Tetrahedron 2011, 67, 4689-4695. J. Colomb, G. Becker, S. Fieux, L. Zimmer, T. Billard, J. Med. Chem. 2014, 57, 3884-3890 B. Boganyi, J. Kaman, Tetrahedron 2013, 69, 9512-9519 P. R. Likhar, M. S. Subhas, S. Roy, M. L. Kantam, B. Sridhar, R. K. Seth, S. Biswas, Org. Biomol. Chem. 2009, 7, 85-93 K. O. Hessian, B. L. Flynn, Org. Lett. 2006, 8, 243-246 X. Ribas, D. A. Jackson, B. Donnadieu, J. Mahìa, T. Parella, R. Xifra, B. Hedman, K. O. Hodgson, A. Llobet, T. D. P. Stack, Angew. Chem. 2002, 114, 3117-3120 D. Maiti, Chem. Commun. 2011, 47, 8340-8342. 2010; 12 2012; 484 2013; 69 2002 2002; 114 41 2004; 25 2014; 68 2014; 24 2011; 54 2013; 70 2011; 13 2015; 80 2007; 36 1944; 35 2014; 20 2013; 18 2014; 768 2010; 66 2009; 52 2014; 4 1982; 28 2012; 133 2012; 134 2013; 54 2013; 56 2002; 43 1996; 61 2014; 16 2013; 156 2014; 57 2011; 67 2007; 63 1998; 54 2009; 323 2010; 75 2015; 17 2015; 5 2012 2011 2015; 51 2015; 97 2013 2013; 125 52 2006; 8 2008; 12 2011; 76 1953; 7 2005 2003 2009; 131 2013; 340 2012; 77 2011; 255 2009 2009; 121 48 2011; 133 2012; 2 2009; 74 2010; 132 2005; 7 2013; 135 2011; 46 2009; 7 2015 2009; 4 2011; 47 1948; 43 2009; 109 2008; 252 2014; 34 e_1_2_6_95_3 e_1_2_6_53_2 e_1_2_6_95_2 e_1_2_6_30_2 e_1_2_6_91_2 e_1_2_6_57_3 e_1_2_6_34_2 e_1_2_6_11_2 e_1_2_6_76_3 e_1_2_6_38_2 e_1_2_6_76_2 e_1_2_6_15_2 e_1_2_6_57_2 e_1_2_6_83_2 e_1_2_6_64_2 e_1_2_6_41_2 e_1_2_6_60_2 e_1_2_6_9_2 e_1_2_6_5_2 e_1_2_6_22_2 e_1_2_6_49_2 e_1_2_6_1_2 Manske R. H. F. (e_1_2_6_20_2) 1953; 7 e_1_2_6_87_2 e_1_2_6_26_2 e_1_2_6_45_2 e_1_2_6_68_2 e_1_2_6_50_2 e_1_2_6_73_2 e_1_2_6_96_2 e_1_2_6_31_2 e_1_2_6_92_2 e_1_2_6_12_2 e_1_2_6_35_2 e_1_2_6_58_2 e_1_2_6_16_2 e_1_2_6_39_2 e_1_2_6_54_2 e_1_2_6_77_2 e_1_2_6_61_2 e_1_2_6_84_2 e_1_2_6_42_2 e_1_2_6_80_2 e_1_2_6_6_2 e_1_2_6_23_2 e_1_2_6_69_2 e_1_2_6_2_2 e_1_2_6_65_2 e_1_2_6_88_2 e_1_2_6_27_2 e_1_2_6_46_2 e_1_2_6_88_3 e_1_2_6_51_2 e_1_2_6_74_2 e_1_2_6_93_2 e_1_2_6_70_2 e_1_2_6_13_2 e_1_2_6_59_2 e_1_2_6_32_2 e_1_2_6_17_2 e_1_2_6_55_2 e_1_2_6_36_2 e_1_2_6_78_2 e_1_2_6_62_2 e_1_2_6_85_2 e_1_2_6_81_2 e_1_2_6_7_2 Cheng C.‐C. (e_1_2_6_19_2) 1982; 28 e_1_2_6_3_2 e_1_2_6_24_2 e_1_2_6_47_2 e_1_2_6_28_2 e_1_2_6_43_2 e_1_2_6_66_2 e_1_2_6_52_2 e_1_2_6_75_2 e_1_2_6_94_2 e_1_2_6_71_2 e_1_2_6_90_2 e_1_2_6_18_2 e_1_2_6_10_2 e_1_2_6_33_2 e_1_2_6_14_2 e_1_2_6_37_2 e_1_2_6_56_2 e_1_2_6_79_2 e_1_2_6_63_2 e_1_2_6_86_2 e_1_2_6_40_2 e_1_2_6_82_2 Phipps R. J. (e_1_2_6_89_2) 2012; 134 Kuijpers B. H. M. (e_1_2_6_72_2) 2005 e_1_2_6_8_2 e_1_2_6_29_2 e_1_2_6_4_2 e_1_2_6_48_2 e_1_2_6_21_2 e_1_2_6_44_2 e_1_2_6_67_2 e_1_2_6_25_2 Ribas, X. (000382968100012.70) 2002; 114 Lord, AM (WOS:000263142400030) 2009; 52 Lal, S (WOS:000338693100023) 2014; 4 Prajapati, SM (WOS:000338042800007) 2014; 4 Madapa, S (WOS:000259447100004) 2008; 12 Balijapalli, U (WOS:000359295800009) 2015; 2015 Garcia-Alvarez, J (WOS:000285682500005) 2010; 12 Cross, RM (WOS:000297946300009) 2011; 54 Majumdar, KC (WOS:000285504500020) 2011 Ryabukhin, SV (WOS:000292480300026) 2011; 76 Zhang, XX (WOS:000274591900002) 2010; 66 Campos, PJ (WOS:000073825300027) 1998; 54 Nilsen, A (WOS:000335879100017) 2014; 57 Keri, RS (WOS:000346354200032) 2014; 68 Jones, RA (WOS:000356734600030) 2015; 97 Crossley, JA (WOS:000280398100077) 2010; 75 Lipunova, GN (WOS:000345073700002) 2014; 34 Hickman, AJ (WOS:000303149900024) 2012; 484 Maiti, D (WOS:000292980900042) 2011; 47 Boganyi, B (WOS:000325388100021) 2013; 69 MANSKE, RHF (WOS:A1953UZ71800002) 1953; 7 Kuijpers, BHM (WOS:000235012400007) 2005 Cahard, E. (000382968100012.13) 2013; 125 Walkinshaw, AJ (WOS:000323876300011) 2013; 135 Sinai, A (WOS:000361087200004) 2015; 17 Colomb, J (WOS:000335879100022) 2014; 57 King, AE (WOS:000281296700055) 2010; 132 CHENG, CC (WOS:A1982QN62900002) 1982; 28 Yum, EK (WOS:000223135900032) 2004; 25 Cahard, E (WOS:000323393100048) 2013; 52 Wang, Y. (000382968100012.77) 2013; 125 Oakdale, JS (WOS:000340902800030) 2014; 20 Tummatorn, J (WOS:000354004600029) 2015; 80 Phipps, RJ (WOS:000264342300035) 2009; 323 Afzal, O (WOS:000356734600058) 2015; 97 Chen, XL (WOS:000300469500021) 2012; 133 REITSEMA, RH (WOS:A1948UE85900002) 1948; 43 Huo, Z (WOS:000274465700030) 2010; 75 Vidal, C (WOS:000338298600016) 2014; 16 Mphahlele, MJ (WOS:000283266200006) 2010; 66 Mphahlele, MJ (WOS:000291778000029) 2011; 67 Hessian, KO (WOS:000234657900017) 2006; 8 Garcia-Alvarez, J (WOS:000312155900011) 2012 Reddy, MS (WOS:000302810800064) 2012; 2 Chen, B (WOS:000291580400013) 2011; 133 Boateng, CA (WOS:000289655100037) 2011; 46 Gorka, AP (WOS:000321884200002) 2013; 56 Khusnutdinov, RI (WOS:000340853500012) 2014; 768 Barluenga, J (WOS:000267893100003) 2009; 4 Huang, H (WOS:000268480300045) 2009; 74 Huma, HZS (WOS:000177617300046) 2002; 43 Mphahlele, MJ (WOS:000280541800014) 2010; 66 Likhar, PR (WOS:000262662000015) 2009; 7 Campos, PJ (WOS:A1996VL34900072) 1996; 61 Worrell, BT (WOS:000318016700036) 2013; 340 Hein, J. E. (000382968100012.31) 2009; 121 Loones, KTJ (WOS:000252091700032) 2007; 63 Yadav, JS (WOS:000184384500023) 2003 Ali, S (WOS:000290465800023) 2011; 13 Franklin, EC (WOS:000187108700001) 1944; 35 Juricek, M (WOS:000291920800053) 2011; 13 Chen, J (WOS:000346897300045) 2015; 51 Phipps, RJ (WOS:000305863900015) 2012; 134 Tumey, LN (WOS:000334337100007) 2014; 24 Zhang, JL (WOS:000349434600061) 2015; 5 Brotherton, WS (WOS:000307037700008) 2012; 77 Nakamura, H (WOS:000237420200034) 2006; 8 Albrecht, M (WOS:000256005000002) 2008; 252 Artizzu, F (WOS:000295768600008) 2011; 255 Hein, JE (WOS:000271130900010) 2009; 48 Bolden, S (WOS:000330554400013) 2013; 70 Wang, Y (WOS:000318370200022) 2013; 52 Zhang, XX (WOS:000227313400004) 2005; 7 Marco-Contelles, J (WOS:000266929800011) 2009; 109 Ribas, X (WOS:000177597700023) 2002; 41 Fu, D. (000382968100012.27) 2013; 156 Mukherjee, S (WOS:000317808300011) 2013; 18 Kuninobu, Y (WOS:000251854700009) 2007; 36 Liu, ZQ (WOS:000344635200024) 2014; 16 Kokatla, HP (WOS:000330097400027) 2013; 56 Colomb, J (WOS:000315306900034) 2013; 54 Chen, WW (WOS:000349943000039) 2015; 80 Bharate, JB (WOS:000354445900083) 2015; 5 Fors, BP (WOS:000265460200023) 2009; 131
References_xml	– reference: J. S. Oakdale, R. K. Sit, V. V. Fokin, Chem. Eur. J. 2014, 20, 11101-11110. – reference: J. Marco-Contelles, E. Perez-Mayoral, A. Samadi, M. C. Carreiras, E. Soriano, Chem. Rev. 2009, 109, 2652-2671; – reference: S. Mukherjee, M. Pal, Drug Discovery Today 2013, 18, 389-398. – reference: O. Afzal, S. Kumar, M. R. Haider, M. R. Ali, R. Kumar, M. Jaggi, S. Bawa, Eur. J. Med. Chem. 2015, 97, 871-910; – reference: Angew. Chem. Int. Ed. 2009, 48, 8018-8021. – reference: J. García-Álverez, J. Díez, J. Gimeno, Green Chem. 2010, 12, 2127-2130. – reference: S. Ali, H.-T. Zhu, X.-F. Xia, K.-G. Ji, Y.-F. Yang, X.-R. Song, Y.-M. Liang, Org. Lett. 2011, 13, 2598-2601; – reference: A. J. Hickman, M. S. Sanford, Nature 2012, 484, 177-185; – reference: F. W. Bergstrom, Chem. Rev. 1944, 35, 77-277. – reference: J. Tummatorn, P. Poonsilp, P. Nimnual, J. Janprasit, C. Thongsornkleeb, S. Ruchirawat, J. Org. Chem. 2015, 80, 4516-4525. – reference: B. P. Fors, N. R. Davis, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 5766-5768; – reference: S. V. Ryabukhin, V. S. Naumchik, A. S. Plaskon, O. O. Grygorenko, A. A. Tolmachev, J. Org. Chem. 2011, 76, 5774-5781; – reference: J. B. Bharate, R. A. Vishwakarma, S. B. Bharate, RSC Adv. 2015, 5, 42020-42053; – reference: Angew. Chem. Int. Ed. 2013, 52, 9284-9288; – reference: E. Cahard, N. Bremeyer, M. J. Gaunt, Angew. Chem. 2013, 125, 9454-9458; – reference: P. J. Campos, E. Anon, M. C. Malo, C.-Q. Tan, M. A. Rodriguez, Tetrahedron 1998, 54, 6929-6938; – reference: A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068-12073; – reference: E. K. Yum, O.-K. Yang, S. K. Kang, H. G. Cheon, S. S. Kim, J.-K. Choi, Bull. Korean Chem. Soc. 2004, 25, 1091-1094; – reference: R. A. Jones, S. S. Panda, C. D. Hall, Eur. J. Med. Chem. 2015, 97, 335-355; – reference: J. Barluenga, F. Rodriguez, F. J. Fananas, Chem. Asian J. 2009, 4, 1036-1048; – reference: D. Maiti, Chem. Commun. 2011, 47, 8340-8342. – reference: U. Balijapalli, S. K. Iyer, Eur. J. Org. Chem. 2015, 5089-5098; – reference: R. I. Khusnutdinov, A. R. Bayguzina, U. M. Dzhemilev, J. Organomet. Chem. 2014, 768, 75-114; – reference: B. Boganyi, J. Kaman, Tetrahedron 2013, 69, 9512-9519; – reference: S. Lal, H. S. Rzepa, S. Díez-González, ACS Catal. 2014, 4, 2274-2287; – reference: R. H. F. Manske, M. Kukla, Org. React. 1953, 7, 59-72; – reference: M. J. Mphahlele, M. M. Mphahlele, Tetrahedron 2011, 67, 4689-4695. – reference: Á. Sinai, D. Vangel, T. Gáti, P. Bombicz, Z. Novák, Org. Lett. 2015, 17, 4136-4139; – reference: A. Nilsen, G. P. Miley, I. P. Forquer, M. W. Mather, K. Katneni, Y. Li, S. Pou, A. M. Pershing, A. M. Stickles, E. Ryan, J. X. Kelly, J. S. Doggett, K. L. White, D. J. Hinrichs, R. W. Winter, S. A. Charman, L. N. Zakharov, I. Bathurst, J. N. Burrows, A. B. Vaidya, M. K. Riscoe, J. Med. Chem. 2014, 57, 3818-3834; – reference: L. N. Tumey, D. H. Boschelli, N. Bhagirath, J. Shim, E. A. Murphy, D. Goodwin, E. M. Bennett, M. Wang, L.-L. Lin, B. Press, M. Shen, R. K. Frisbie, P. Morgan, S. Mohan, J. Shin, V. R. Rao, Bioorg. Med. Chem. Lett. 2014, 24, 2066-2072; – reference: K. C. Majumdar, R. K. Nandi, S. Ganai, A, Taher, Synlett 2011, 116-120; – reference: A.-M. Lord, M. F. Mahon, M. D. Lloyd, M. D. Threadgill, J. Med. Chem. 2009, 52, 868-877; – reference: J. Zhang, W. Chen, B. Wang, Z. Zhao, X. Wang, Y. Hu, RSC Adv. 2015, 5, 14561-14566; – reference: D. Fu, J. Zhang, S. Cao, J. Fluorine Chem. 2013, 156, 170-176; – reference: C. Vidal, J. Darcía-Álvarez, Green Chem. 2014, 16, 3515-3521; – reference: A. P. Gorka, A. de Dios, P. D. Roepe, J. Med. Chem. 2013, 56, 5231-5246; – reference: G. N. Lipunova, E. V. Nosova, V. N. Charushin, O. N. Chupakhin, Comment Inorg. Chem. 2014, 34, 142-177; – reference: Z. Huo, I. D. Gridnev, Y. Yamamoto, J. Org. Chem. 2010, 75, 1266-1270; – reference: W. Chen, J. Zhang, B. Wang, Z. Zhao, X. Wang, Y. Hu, J. Org. Chem. 2015, 80, 2413-2417; – reference: S. M. Prajapati, K. D. Patel, R. H. Vekariya, S. N. Panchal, H. D. Patel, RSC Adv. 2014, 4, 24463-24476; – reference: B. H. M. Kuijpers, G. C. T. Dijkmans, S. Groothuys, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Synlett 2005, 3059-3062. – reference: Angew. Chem. Int. Ed. 2002, 41, 2991-2994. – reference: K. O. Hessian, B. L. Flynn, Org. Lett. 2006, 8, 243-246; – reference: X. Ribas, D. A. Jackson, B. Donnadieu, J. Mahìa, T. Parella, R. Xifra, B. Hedman, K. O. Hodgson, A. Llobet, T. D. P. Stack, Angew. Chem. 2002, 114, 3117-3120; – reference: Angew. Chem. Int. Ed. 2013, 52, 5323-5327; – reference: X.-L. Chen, J.-M. Zhang, W.-L. Shang, B.-Q. Lu, J.-A. Jin, J. Fluorine Chem. 2012, 133, 139-145; – reference: X. Zhang, T. Yao, M. A. Campo, R. C. Larock, Tetrahedron 2010, 66, 1177-1187; – reference: S. Madapa, Z. Tusi, S. Batra, Curr. Org. Chem. 2008, 12, 1116-1183. – reference: P. R. Likhar, M. S. Subhas, S. Roy, M. L. Kantam, B. Sridhar, R. K. Seth, S. Biswas, Org. Biomol. Chem. 2009, 7, 85-93; – reference: H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, J. Iqbala, Tetrahedron Lett. 2002, 43, 6485-6488. – reference: A. J. Walkinshaw, W. Xu, M. G. Suero, M. J. Gaunt, J. Am. Chem. Soc. 2013, 135, 12532-12535; – reference: J. E. Hein, J. C. Tripp, L. B. Krasnova, K. B. Sharpless, V. V. Fokin, Angew. Chem. 2009, 121, 8162-8165; – reference: J. A. Crossley, D. L. Browne, J. Org. Chem. 2010, 75, 5414-5416. – reference: H. Huang, H. Jiang, K. Chen, H. Liu, J. Org. Chem. 2009, 74, 5476-5480; – reference: R. M. Cross, N. K. Namelikonda, T. S. Mutka, L. Luong, D. E. Kyle, R. Manetsch, J. Med. Chem. 2011, 54, 8321-8327; – reference: Y. Kuninobu, Y. Inoue, K. Takai, Chem. Lett. 2007, 36, 1422-1423; – reference: M. Albrecht, M. Fiege, O. Osetska, Coord. Chem. Rev. 2008, 252, 812-824. – reference: R. S. Keri, S. A. Patil, Biomed. Pharmacother. 2014, 68, 1161-1175; – reference: M. J. Mphahlele, Tetrahedron 2010, 66, 8261-8266. – reference: H. Nakamura, T. Kamakura, S. Onagi, Org. Lett. 2006, 8, 2095-2098. – reference: S. Bolden Jr, X. Y. Zhu, J. R. Etukala, C. Boateng, T. Mazu, H. Flores-Rozas, M. R. Jacob, S. I. Khan, L. A. Walker, S. Y. Ablordeppey, Eur. J. Med. Chem. 2013, 70, 130-142; – reference: W. S. Brotherton, R. J. Clark, L. Zhu, J. Org. Chem. 2012, 77, 6443-6455; – reference: J. Colomb, T. Billard, Tetrahedron Lett. 2013, 54, 1471-1474; – reference: C. A. Boateng, X. Y. Zhu, M. R. Jacob, S. I. Khan, L. A. Walker, S. Y. Ablordeppey, Eur. J. Med. Chem. 2011, 46, 1789-1797. – reference: B. T. Worrell, J. A. Malik, V. V. Fokin, Science 2013, 340, 457-460; – reference: R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593-1597; – reference: H. P. Kokatla, D. Sil, S. S. Malladi, R. Balakrishna, A. R. Hermanson, L. M. Fox, X. Wang, A. Dixit, S. A. David, J. Med. Chem. 2013, 56, 6871-6885; – reference: M. Juríček, K. Stout, P. H. Kouwer, A. E. Rowan, Org. Lett. 2011, 13, 3494-3497; – reference: F. Artizzu, M. L. Mercuri, A. Serpe, P. Deplano, Coord. Chem. Rev. 2011, 255, 2514-2529; – reference: X. Zhang, M. A. Campo, T. Yao, R. C. Larock, Org. Lett. 2005, 7, 763-766; – reference: M. S. Reddy, N. Thirupathi, Y. K. Kumar, RSC Adv. 2012, 2, 3986-3992; – reference: J. S. Yadav, B. V. S. Reddy, R. S. Rao, V. Naveenkumar, K, Nagaiah, Synthesis 2003, 1610-1614; – reference: P. J. Campos, C.-Q. Tan, M. A. Rodriguez, E. Anon, J. Org. Chem. 1996, 61, 7195-7197. – reference: Y. Wang, C. Chen, J. Peng, M. Li, Angew. Chem. 2013, 125, 5431-5435; – reference: Z. Liu, D. Zhu, B. Luo, N. Zhang, Q. Liu, Y. Hu, R. Pi, P. Huang, S. Wen, Org. Lett. 2014, 16, 5600-5603; – reference: K. T. J. Loones, B. U. W. Maes, R. A. Dommisse, Tetrahedron 2007, 63, 8954-8961. – reference: J. Colomb, G. Becker, S. Fieux, L. Zimmer, T. Billard, J. Med. Chem. 2014, 57, 3884-3890; – reference: J. García-Álverez, J. Díez, J. Gimeno, F. J. Suárez, C. Vincent, Eur. J. Inorg. Chem. 2012, 5854-5863; – reference: M. J. Mphahlele, L. G. Lesenyeho, H. R. Makelane, Tetrahedron 2010, 66, 6040-6046; – reference: R. J. Phipps, L. McMurray, S. Ritter, H. A. Duong, M. J. Gaunt, J. Am. Chem. Soc. 2012, 134, 1073-10776. – reference: B. Chen, X.-L. Hou, Y.-X. Li, Y.-D. Wu, J. Am. Chem. Soc. 2011, 133, 7668-7671; – reference: R. H. Reitsema, Chem. Rev. 1948, 43, 47-68; – reference: J. Chen, C. Chen, J. Chen, G. Wang, H. Qu, Chem. Commun. 2015, 51, 1356-1359; – reference: C.-C. Cheng, S.-J. Yan, Org. React. 1982, 28, 37-201; – volume: 7 start-page: 59 year: 1953 end-page: 72 publication-title: Org. React. – volume: 46 start-page: 1789 year: 2011 end-page: 1797 publication-title: Eur. J. Med. Chem. – volume: 132 start-page: 12068 year: 2010 end-page: 12073 publication-title: J. Am. Chem. Soc. – volume: 16 start-page: 3515 year: 2014 end-page: 3521 publication-title: Green Chem. – volume: 36 start-page: 1422 year: 2007 end-page: 1423 publication-title: Chem. Lett. – volume: 67 start-page: 4689 year: 2011 end-page: 4695 publication-title: Tetrahedron – volume: 8 start-page: 243 year: 2006 end-page: 246 publication-title: Org. Lett. – start-page: 5854 year: 2012 end-page: 5863 publication-title: Eur. J. Inorg. Chem. – volume: 20 start-page: 11101 year: 2014 end-page: 11110 publication-title: Chem. Eur. J. – volume: 323 start-page: 1593 year: 2009 end-page: 1597 publication-title: Science – volume: 80 start-page: 2413 year: 2015 end-page: 2417 publication-title: J. Org. Chem. – volume: 51 start-page: 1356 year: 2015 end-page: 1359 publication-title: Chem. Commun. – volume: 75 start-page: 1266 year: 2010 end-page: 1270 publication-title: J. Org. Chem. – volume: 16 start-page: 5600 year: 2014 end-page: 5603 publication-title: Org. Lett. – start-page: 1610 year: 2003 end-page: 1614 publication-title: Synthesis – volume: 4 start-page: 2274 year: 2014 end-page: 2287 publication-title: ACS Catal. – volume: 114 41 start-page: 3117 2991 year: 2002 2002 end-page: 3120 2994 publication-title: Angew. Chem. Angew. Chem. Int. Ed. – volume: 133 start-page: 139 year: 2012 end-page: 145 publication-title: J. Fluorine Chem. – volume: 131 start-page: 5766 year: 2009 end-page: 5768 publication-title: J. Am. Chem. Soc. – volume: 66 start-page: 1177 year: 2010 end-page: 1187 publication-title: Tetrahedron – start-page: 3059 year: 2005 end-page: 3062 publication-title: Synlett – volume: 484 start-page: 177 year: 2012 end-page: 185 publication-title: Nature – volume: 252 start-page: 812 year: 2008 end-page: 824 publication-title: Coord. Chem. Rev. – volume: 54 start-page: 6929 year: 1998 end-page: 6938 publication-title: Tetrahedron – volume: 5 start-page: 42020 year: 2015 end-page: 42053 publication-title: RSC Adv. – volume: 70 start-page: 130 year: 2013 end-page: 142 publication-title: Eur. J. Med. Chem. – volume: 76 start-page: 5774 year: 2011 end-page: 5781 publication-title: J. Org. Chem. – volume: 77 start-page: 6443 year: 2012 end-page: 6455 publication-title: J. Org. Chem. – volume: 57 start-page: 3884 year: 2014 end-page: 3890 publication-title: J. Med. Chem. – volume: 255 start-page: 2514 year: 2011 end-page: 2529 publication-title: Coord. Chem. Rev. – volume: 7 start-page: 763 year: 2005 end-page: 766 publication-title: Org. Lett. – volume: 25 start-page: 1091 year: 2004 end-page: 1094 publication-title: Bull. Korean Chem. Soc. – volume: 5 start-page: 14561 year: 2015 end-page: 14566 publication-title: RSC Adv. – volume: 43 start-page: 47 year: 1948 end-page: 68 publication-title: Chem. Rev. – volume: 8 start-page: 2095 year: 2006 end-page: 2098 publication-title: Org. Lett. – volume: 121 48 start-page: 8162 8018 year: 2009 2009 end-page: 8165 8021 publication-title: Angew. Chem. Angew. Chem. Int. Ed. – volume: 13 start-page: 3494 year: 2011 end-page: 3497 publication-title: Org. Lett. – volume: 35 start-page: 77 year: 1944 end-page: 277 publication-title: Chem. Rev. – volume: 57 start-page: 3818 year: 2014 end-page: 3834 publication-title: J. Med. Chem. – volume: 340 start-page: 457 year: 2013 end-page: 460 publication-title: Science – volume: 125 52 start-page: 9454 9284 year: 2013 2013 end-page: 9458 9288 publication-title: Angew. Chem. Angew. Chem. Int. Ed. – volume: 133 start-page: 7668 year: 2011 end-page: 7671 publication-title: J. Am. Chem. Soc. – volume: 24 start-page: 2066 year: 2014 end-page: 2072 publication-title: Bioorg. Med. Chem. Lett. – volume: 69 start-page: 9512 year: 2013 end-page: 9519 publication-title: Tetrahedron – volume: 63 start-page: 8954 year: 2007 end-page: 8961 publication-title: Tetrahedron – volume: 80 start-page: 4516 year: 2015 end-page: 4525 publication-title: J. Org. Chem. – volume: 52 start-page: 868 year: 2009 end-page: 877 publication-title: J. Med. Chem. – volume: 156 start-page: 170 year: 2013 end-page: 176 publication-title: J. Fluorine Chem. – volume: 97 start-page: 335 year: 2015 end-page: 355 publication-title: Eur. J. Med. Chem. – volume: 768 start-page: 75 year: 2014 end-page: 114 publication-title: J. Organomet. Chem. – volume: 66 start-page: 8261 year: 2010 end-page: 8266 publication-title: Tetrahedron – volume: 13 start-page: 2598 year: 2011 end-page: 2601 publication-title: Org. Lett. – volume: 56 start-page: 6871 year: 2013 end-page: 6885 publication-title: J. Med. Chem. – volume: 135 start-page: 12532 year: 2013 end-page: 12535 publication-title: J. Am. Chem. Soc. – volume: 61 start-page: 7195 year: 1996 end-page: 7197 publication-title: J. Org. Chem. – volume: 12 start-page: 2127 year: 2010 end-page: 2130 publication-title: Green Chem. – volume: 18 start-page: 389 year: 2013 end-page: 398 publication-title: Drug Discovery Today – volume: 4 start-page: 24463 year: 2014 end-page: 24476 publication-title: RSC Adv. – volume: 56 start-page: 5231 year: 2013 end-page: 5246 publication-title: J. Med. Chem. – volume: 43 start-page: 6485 year: 2002 end-page: 6488 publication-title: Tetrahedron Lett. – volume: 75 start-page: 5414 year: 2010 end-page: 5416 publication-title: J. Org. Chem. – volume: 47 start-page: 8340 year: 2011 end-page: 8342 publication-title: Chem. Commun. – start-page: 116 year: 2011 end-page: 120 publication-title: Synlett – volume: 134 start-page: 1073 year: 2012 end-page: 10776 publication-title: J. Am. Chem. Soc. – volume: 2 start-page: 3986 year: 2012 end-page: 3992 publication-title: RSC Adv. – start-page: 5089 year: 2015 end-page: 5098 publication-title: Eur. J. Org. Chem. – volume: 34 start-page: 142 year: 2014 end-page: 177 publication-title: Comment Inorg. Chem. – volume: 17 start-page: 4136 year: 2015 end-page: 4139 publication-title: Org. Lett. – volume: 125 52 start-page: 5431 5323 year: 2013 2013 end-page: 5435 5327 publication-title: Angew. Chem. Angew. Chem. Int. Ed. – volume: 74 start-page: 5476 year: 2009 end-page: 5480 publication-title: J. Org. Chem. – volume: 28 start-page: 37 year: 1982 end-page: 201 publication-title: Org. React. – volume: 4 start-page: 1036 year: 2009 end-page: 1048 publication-title: Chem. Asian J. – volume: 12 start-page: 1116 year: 2008 end-page: 1183 publication-title: Curr. Org. Chem. – volume: 66 start-page: 6040 year: 2010 end-page: 6046 publication-title: Tetrahedron – volume: 7 start-page: 85 year: 2009 end-page: 93 publication-title: Org. Biomol. Chem. – volume: 54 start-page: 1471 year: 2013 end-page: 1474 publication-title: Tetrahedron Lett. – volume: 68 start-page: 1161 year: 2014 end-page: 1175 publication-title: Biomed. Pharmacother. – volume: 54 start-page: 8321 year: 2011 end-page: 8327 publication-title: J. Med. Chem. – volume: 97 start-page: 871 year: 2015 end-page: 910 publication-title: Eur. J. Med. Chem. – volume: 109 start-page: 2652 year: 2009 end-page: 2671 publication-title: Chem. Rev. – ident: e_1_2_6_80_2 doi: 10.1246/cl.2007.1422 – ident: e_1_2_6_83_2 – ident: e_1_2_6_22_2 doi: 10.1021/cr60111a001 – ident: e_1_2_6_77_2 doi: 10.1016/j.jfluchem.2011.08.005 – ident: e_1_2_6_93_2 doi: 10.1021/ja1045378 – ident: e_1_2_6_78_2 doi: 10.1055/s-0030-1259097 – ident: e_1_2_6_3_2 doi: 10.1016/j.ejmech.2015.02.002 – ident: e_1_2_6_32_2 doi: 10.1021/jm500147k – ident: e_1_2_6_35_2 doi: 10.1021/jm200718m – ident: e_1_2_6_40_2 doi: 10.1016/j.tet.2007.06.011 – ident: e_1_2_6_10_2 doi: 10.1016/j.ccr.2007.06.003 – ident: e_1_2_6_96_2 – ident: e_1_2_6_24_2 doi: 10.1021/jm8013629 – ident: e_1_2_6_15_2 doi: 10.1002/asia.200900018 – ident: e_1_2_6_12_2 doi: 10.1039/C5RA07798B – ident: e_1_2_6_67_2 doi: 10.1039/c0gc00342e – ident: e_1_2_6_68_2 – ident: e_1_2_6_44_2 doi: 10.1016/j.ejmech.2013.09.044 – ident: e_1_2_6_95_3 doi: 10.1002/1521-3773(20020816)41:16<2991::AID-ANIE2991>3.0.CO;2-6 – ident: e_1_2_6_56_2 doi: 10.1021/jo9600215 – ident: e_1_2_6_49_2 doi: 10.1021/jo2008252 – ident: e_1_2_6_79_2 doi: 10.1021/jo901101v – ident: e_1_2_6_51_2 doi: 10.1021/jo902603v – ident: e_1_2_6_64_2 doi: 10.1021/jo300841c – ident: e_1_2_6_60_2 doi: 10.1039/c4gc00451e – ident: e_1_2_6_17_2 – ident: e_1_2_6_28_2 doi: 10.1021/jm400694d – ident: e_1_2_6_48_2 doi: 10.1021/ol2007154 – ident: e_1_2_6_61_2 doi: 10.1021/cs500326e – ident: e_1_2_6_54_2 doi: 10.1021/ol0476218 – ident: e_1_2_6_43_2 doi: 10.1021/jm500372e – ident: e_1_2_6_8_2 doi: 10.1080/02603594.2014.959116 – ident: e_1_2_6_94_2 doi: 10.1126/science.1169975 – ident: e_1_2_6_50_2 doi: 10.1016/j.tet.2009.12.012 – ident: e_1_2_6_95_2 doi: 10.1002/1521-3757(20020816)114:16<3117::AID-ANGE3117>3.0.CO;2-U – ident: e_1_2_6_23_2 – ident: e_1_2_6_42_2 – ident: e_1_2_6_33_2 doi: 10.1016/j.bmcl.2014.03.056 – ident: e_1_2_6_36_2 doi: 10.1016/j.tet.2011.04.040 – ident: e_1_2_6_38_2 doi: 10.1016/j.tet.2013.08.019 – ident: e_1_2_6_65_2 doi: 10.1002/ejic.201200789 – ident: e_1_2_6_1_2 – ident: e_1_2_6_7_2 – ident: e_1_2_6_5_2 doi: 10.1021/jm400282d – ident: e_1_2_6_75_2 doi: 10.1002/ejoc.201500461 – volume: 28 start-page: 37 year: 1982 ident: e_1_2_6_19_2 publication-title: Org. React. – ident: e_1_2_6_57_3 doi: 10.1002/anie.200903558 – ident: e_1_2_6_58_2 – volume: 134 start-page: 1073 year: 2012 ident: e_1_2_6_89_2 publication-title: J. Am. Chem. Soc. – ident: e_1_2_6_87_2 doi: 10.1021/ja405972h – ident: e_1_2_6_27_2 – ident: e_1_2_6_13_2 doi: 10.1039/C4RA01814A – ident: e_1_2_6_63_2 doi: 10.1016/j.jfluchem.2013.10.006 – ident: e_1_2_6_41_2 doi: 10.1039/c1cc12694f – ident: e_1_2_6_4_2 doi: 10.1016/j.biopha.2014.10.007 – ident: e_1_2_6_29_2 doi: 10.1016/j.tet.2010.06.018 – ident: e_1_2_6_74_2 – ident: e_1_2_6_53_2 doi: 10.1021/ol052518j – ident: e_1_2_6_52_2 doi: 10.1039/B815398A – ident: e_1_2_6_57_2 doi: 10.1002/ange.200903558 – ident: e_1_2_6_30_2 doi: 10.1016/j.tet.2010.08.043 – ident: e_1_2_6_18_2 doi: 10.1021/cr800482c – ident: e_1_2_6_71_2 doi: 10.1021/acs.joc.5b00375 – ident: e_1_2_6_73_2 doi: 10.1002/chem.201402559 – ident: e_1_2_6_92_2 doi: 10.1021/ja201425e – ident: e_1_2_6_81_2 doi: 10.1055/s-2003-40531 – ident: e_1_2_6_82_2 doi: 10.1016/S0040-4039(02)01240-6 – ident: e_1_2_6_45_2 doi: 10.1016/j.ejmech.2011.02.034 – ident: e_1_2_6_90_2 – ident: e_1_2_6_11_2 – ident: e_1_2_6_86_2 doi: 10.1021/ol502654a – start-page: 3059 year: 2005 ident: e_1_2_6_72_2 publication-title: Synlett – ident: e_1_2_6_9_2 doi: 10.1016/j.ccr.2011.01.013 – volume: 7 start-page: 59 year: 1953 ident: e_1_2_6_20_2 publication-title: Org. React. – ident: e_1_2_6_26_2 doi: 10.1021/ol060538v – ident: e_1_2_6_47_2 doi: 10.1039/c2ra20213a – ident: e_1_2_6_6_2 doi: 10.1016/j.drudis.2012.11.003 – ident: e_1_2_6_69_2 doi: 10.1021/jo502634h – ident: e_1_2_6_46_2 – ident: e_1_2_6_39_2 doi: 10.1021/ja901414u – ident: e_1_2_6_25_2 doi: 10.5012/bkcs.2004.25.7.1091 – ident: e_1_2_6_62_2 doi: 10.1126/science.1229506 – ident: e_1_2_6_76_3 doi: 10.1002/anie.201300586 – ident: e_1_2_6_91_2 doi: 10.1038/nature11008 – ident: e_1_2_6_59_2 doi: 10.1039/C4RA15980B – ident: e_1_2_6_88_2 doi: 10.1002/ange.201303724 – ident: e_1_2_6_66_2 doi: 10.1021/ol201290q – ident: e_1_2_6_31_2 – ident: e_1_2_6_16_2 doi: 10.2174/138527208785740300 – ident: e_1_2_6_70_2 doi: 10.1021/jo1011174 – ident: e_1_2_6_76_2 doi: 10.1002/ange.201300586 – ident: e_1_2_6_85_2 doi: 10.1039/C4CC08363F – ident: e_1_2_6_21_2 doi: 10.1021/cr60134a002 – ident: e_1_2_6_55_2 doi: 10.1016/S0040-4020(98)00374-3 – ident: e_1_2_6_37_2 – ident: e_1_2_6_88_3 doi: 10.1002/anie.201303724 – ident: e_1_2_6_84_2 doi: 10.1021/acs.orglett.5b01860 – ident: e_1_2_6_14_2 doi: 10.1016/j.jorganchem.2014.06.008 – ident: e_1_2_6_34_2 doi: 10.1016/j.tetlet.2013.01.018 – ident: e_1_2_6_2_2 doi: 10.1016/j.ejmech.2014.07.044 – start-page: 116 year: 2011 ident: WOS:000285504500020 article-title: Regioselective Synthesis of Annulated Quinoline and Pyridine Derivatives by Silver-Catalyzed 6-endo-dig Cycloisomerization publication-title: SYNLETT doi: 10.1055/s-0030-1259097 – volume: 52 start-page: 868 year: 2009 ident: WOS:000263142400030 article-title: Design, Synthesis, and Evaluation in Vitro of Quinoline-8-carboxamides, a New Class of Poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) Inhibitor publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm8013629 – volume: 57 start-page: 3818 year: 2014 ident: WOS:000335879100017 article-title: Discovery, Synthesis, and Optimization of Antimalarial 4(1H)-Quinolone-3-Diarylethers publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm500147k – volume: 2 start-page: 3986 year: 2012 ident: WOS:000302810800064 article-title: A quick and efficient route to substituted quinolines by electrophilic cyclization of 1-(2-aminoaryl)-2-yn-1-ols publication-title: RSC ADVANCES doi: 10.1039/c2ra20213a – volume: 8 start-page: 2095 year: 2006 ident: WOS:000237420200034 article-title: 1,2-Bis(diphenylphosphino)carborane as a dual mode ligand for both the sonogashira coupling and hydride-transfer steps in palladium-catalyzed one-pot synthesis of allenes from aryl iodides publication-title: ORGANIC LETTERS doi: 10.1021/ol060538v – volume: 484 start-page: 177 year: 2012 ident: WOS:000303149900024 article-title: High-valent organometallic copper and palladium in catalysis publication-title: NATURE doi: 10.1038/nature11008 – volume: 4 start-page: 2274 year: 2014 ident: WOS:000338693100023 article-title: Catalytic and Computational Studies of N-Heterocyclic Carbene or Phosphine-Containing Copper(I) Complexes for the Synthesis of 5-lodo-1,2,3-Triazoles publication-title: ACS CATALYSIS doi: 10.1021/cs500326e – volume: 54 start-page: 1471 year: 2013 ident: WOS:000315306900034 article-title: Palladium-catalyzed desulfitative arylation of 3-haloquinolines with arylsulfinates publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2013.01.018 – volume: 2015 start-page: 5089 year: 2015 ident: WOS:000359295800009 article-title: Synthesis and Optical Properties of a Series of Green-Light-Emitting 2-(4-Phenylquinolin-2-yl)phenol-BF2 Complexes (Boroquinols) publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201500461 – volume: 125 start-page: 5431 year: 2013 ident: 000382968100012.77 publication-title: Angew. Chem – volume: 131 start-page: 5766 year: 2009 ident: WOS:000265460200023 article-title: An Efficient Process for Pd-Catalyzed C-N Cross-Coupling Reactions of Aryl Iodides: Insight Into Controlling Factors publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja901414u – volume: 69 start-page: 9512 year: 2013 ident: WOS:000325388100021 article-title: A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions publication-title: TETRAHEDRON doi: 10.1016/j.tet.2013.08.019 – volume: 48 start-page: 8018 year: 2009 ident: WOS:000271130900010 article-title: Copper(I)-Catalyzed Cycloaddition of Organic Azides and 1-Iodoalkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200903558 – volume: 7 start-page: 85 year: 2009 ident: WOS:000262662000015 article-title: Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/b815398a – volume: 54 start-page: 6929 year: 1998 ident: WOS:000073825300027 article-title: Synthesis of substituted benzoquinolines by the irradiation of 3-amino-2-alkene imines publication-title: TETRAHEDRON – volume: 7 start-page: 763 year: 2005 ident: WOS:000227313400004 article-title: Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl)anilines publication-title: ORGANIC LETTERS doi: 10.1021/ol0476218 – volume: 18 start-page: 389 year: 2013 ident: WOS:000317808300011 article-title: Quinolines: a new hope against inflammation publication-title: DRUG DISCOVERY TODAY doi: 10.1016/j.drudis.2012.11.003 – volume: 12 start-page: 2127 year: 2010 ident: WOS:000285682500005 article-title: A highly efficient copper(I) catalyst for the 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes in water: regioselective synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles publication-title: GREEN CHEMISTRY doi: 10.1039/c0gc00342e – volume: 768 start-page: 75 year: 2014 ident: WOS:000340853500012 article-title: Metal complex catalysis in the synthesis of quinolines publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY doi: 10.1016/j.jorganchem.2014.06.008 – volume: 46 start-page: 1789 year: 2011 ident: WOS:000289655100037 article-title: Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2011.02.034 – volume: 114 start-page: 3117 year: 2002 ident: 000382968100012.70 publication-title: Angew. Chem. – volume: 25 start-page: 1091 year: 2004 ident: WOS:000223135900032 article-title: Synthesis of 4-phenylamino-3-vinylquinoline derivatives as gastric H+/K+-ATPase inhibitors publication-title: BULLETIN OF THE KOREAN CHEMICAL SOCIETY – volume: 133 start-page: 7668 year: 2011 ident: WOS:000291580400013 article-title: Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C-H Bond Arylation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja201425e – volume: 56 start-page: 5231 year: 2013 ident: WOS:000321884200002 article-title: Quinoline Drug-Heme Interactions and Implications for Antimalarial Cytostatic versus Cytocidal Activities publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm400282d – volume: 97 start-page: 871 year: 2015 ident: WOS:000356734600058 article-title: A review on anticancer potential of bioactive heterocycle quinoline publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2014.07.044 – start-page: 3059 year: 2005 ident: WOS:000235012400007 article-title: Copper(I)-mediated synthesis of trisubstituted 1,2,3-triazoles publication-title: SYNLETT doi: 10.1055/s-2005-921919 – volume: 34 start-page: 142 year: 2014 ident: WOS:000345073700002 article-title: Structural, Optical Properties, and Biological Activity of Complexes Based on Derivatives of Quinoline, Quinoxaline, and Quinazoline with Metal Centers from Across the Periodic Table publication-title: COMMENTS ON INORGANIC CHEMISTRY doi: 10.1080/02603594.2014.959116 – volume: 5 start-page: 14561 year: 2015 ident: WOS:000349434600061 article-title: One-pot three-component synthesis of 1,4,5-trisubstituted 5-iodo-1,2,3-triazoles from 1-copper( I) alkyne, azide and molecular iodine publication-title: RSC ADVANCES doi: 10.1039/c4ra15980b – start-page: 1610 year: 2003 ident: WOS:000184384500023 article-title: Microwave-assisted one-pot synthesis of 2,4-disubstituted quinolines under solvent-free conditions publication-title: SYNTHESIS-STUTTGART – volume: 13 start-page: 3494 year: 2011 ident: WOS:000291920800053 article-title: Fusing Triazoles: Toward Extending Aromaticity publication-title: ORGANIC LETTERS doi: 10.1021/ol201290q – volume: 75 start-page: 5414 year: 2010 ident: WOS:000280398100077 article-title: An Alkynyliodide Cycloaddition Strategy for the Construction of Iodoisoxazoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo1011174 – volume: 28 start-page: 37 year: 1982 ident: WOS:A1982QN62900002 article-title: THE FRIEDLANDER SYNTHESIS OF QUINOLINES publication-title: ORGANIC REACTIONS – volume: 80 start-page: 2413 year: 2015 ident: WOS:000349943000039 article-title: Tandem Synthesis of 3-Chloro-4-iodoisoxazoles from 1-Copper(I) Alkynes, Dichloroformaldoxime, and Molecular Iodine publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo502634h – volume: 41 start-page: 2991 year: 2002 ident: WOS:000177597700023 article-title: Aryl C-H activation by Cu-II to form an organometallic Aryl-Cu-III species: A novel twist on copper disproportionation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 52 start-page: 9284 year: 2013 ident: WOS:000323393100048 article-title: Copper-Catalyzed Intramolecular Electrophilic Carbofunctionalization of Allylic Amides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201303724 – volume: 132 start-page: 12068 year: 2010 ident: WOS:000281296700055 article-title: Copper-Catalyzed Aerobic Oxidative Functionalization of an Arene C-H Bond: Evidence for an Aryl-Copper(III) Intermediate publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja1045378 – volume: 4 start-page: 1036 year: 2009 ident: WOS:000267893100003 article-title: Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions publication-title: CHEMISTRY-AN ASIAN JOURNAL doi: 10.1002/asia.200900018 – volume: 63 start-page: 8954 year: 2007 ident: WOS:000252091700032 article-title: Synthesis of pyrido[2 ',1 ': 2,3]imidazo[4,5-b] quinoline and pyrido[1 ',2 ': 1,2]imidazo[4,5-b]quinoline and their benzo and aza analogs via tandem catalysis publication-title: TETRAHEDRON doi: 10.1016/j.tet.2007.06.011 – volume: 135 start-page: 12532 year: 2013 ident: WOS:000323876300011 article-title: Copper-Catalyzed Carboarylation of Alkynes via Vinyl Cations publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja405972h – volume: 77 start-page: 6443 year: 2012 ident: WOS:000307037700008 article-title: Synthesis of 5-lodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ Generated Copper(I) Catalyst and Electrophilic Triiodide Ion publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo300841c – start-page: 5854 year: 2012 ident: WOS:000312155900011 article-title: (Iminophosphorane)copper(I) Complexes as Highly Efficient Catalysts for 1,3-Dipolar Cycloaddition of Azides with Terminal and 1-Iodoalkynes in Water: One-Pot Multi-Component Reaction from Alkynes and in situ Generated Azides publication-title: EUROPEAN JOURNAL OF INORGANIC CHEMISTRY doi: 10.1002/ejic.201200789 – volume: 8 start-page: 243 year: 2006 ident: WOS:000234657900017 article-title: Selective endo and exo iodocyclizations in the synthesis of Quinolines and Indoles publication-title: ORGANIC LETTERS doi: 10.1021/ol052518j – volume: 43 start-page: 43 year: 1948 ident: WOS:A1948UE85900002 article-title: THE CHEMISTRY OF 4-HYDROXYQUINOLINES publication-title: CHEMICAL REVIEWS – volume: 61 start-page: 7195 year: 1996 ident: WOS:A1996VL34900072 article-title: Preparation of 3-haloquinolines from 3-amino-2-halo-2-alkenimines publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 36 start-page: 1422 year: 2007 ident: WOS:000251854700009 article-title: Copper(I)- and gold(I)-catalyzed synthesis of 2,4-disubstituted quinoline derivatives from N-aryl-2-propynylamines publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.2007.1422 – volume: 97 start-page: 335 year: 2015 ident: WOS:000356734600030 article-title: Quinine conjugates and quinine analogues as potential antimalarial agents publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2015.02.002 – volume: 133 start-page: 139 year: 2012 ident: WOS:000300469500021 article-title: Microwave promoted one-pot preparation of fluorinated propargylamines and their chemical transformation publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2011.08.005 – volume: 66 start-page: 8261 year: 2010 ident: WOS:000283266200006 article-title: Regioselective alkynylation of 2-aryl-4-chloro-3-iodoquinolines and subsequent arylation or amination of the 2-aryl-3-(alkynyl)-4-chloroquinolines publication-title: TETRAHEDRON doi: 10.1016/j.tet.2010.08.043 – volume: 13 start-page: 2598 year: 2011 ident: WOS:000290465800023 article-title: Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines publication-title: ORGANIC LETTERS doi: 10.1021/ol2007154 – volume: 156 start-page: 170 year: 2013 ident: 000382968100012.27 publication-title: J. Fluorine Chem – volume: 67 start-page: 4689 year: 2011 ident: WOS:000291778000029 article-title: One-pot palladium-catalyzed C-I and C-H bond activation and subsequent Suzuki-Miyaura cross-coupling of 2-aryl-3-iodo-4-(phenylamino)quinolines with arylboronic acids publication-title: TETRAHEDRON doi: 10.1016/j.tet.2011.04.040 – volume: 35 start-page: 77 year: 1944 ident: WOS:000187108700001 article-title: Heterocyclic nitrogen compounds - Part II A. Hexacyclic compounds: Pyridine, quinoline, and isoquinoline publication-title: CHEMICAL REVIEWS – volume: 52 start-page: 5323 year: 2013 ident: WOS:000318370200022 article-title: Copper(II)-Catalyzed Three-Component Cascade Annulation of Diaryliodoniums, Nitriles, and Alkynes: A Regioselective Synthesis of Multiply Substituted Quinolines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201300586 – volume: 4 start-page: 24463 year: 2014 ident: WOS:000338042800007 article-title: Recent advances in the synthesis of quinolines: a review publication-title: RSC ADVANCES doi: 10.1039/c4ra01814a – volume: 109 start-page: 2652 year: 2009 ident: WOS:000266929800011 article-title: Recent Advances in the Friedlander Reaction publication-title: CHEMICAL REVIEWS doi: 10.1021/cr800482c – volume: 51 start-page: 1356 year: 2015 ident: WOS:000346897300045 article-title: Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl alkynes with diaryliodonium salts via cleavage of a stable C-O bond publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc08363f – volume: 125 start-page: 9454 year: 2013 ident: 000382968100012.13 publication-title: Angew. Chem – volume: 16 start-page: 5600 year: 2014 ident: WOS:000344635200024 article-title: Mild Cu(I)-Catalyzed Cascade Reaction of Cyclic Diaryliodoniums, Sodium Azide, and Alkynes: Efficient Synthesis of Triazolophenanthridines publication-title: ORGANIC LETTERS doi: 10.1021/ol502654a – volume: 66 start-page: 1177 year: 2010 ident: WOS:000274591900002 article-title: Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines publication-title: TETRAHEDRON doi: 10.1016/j.tet.2009.12.012 – volume: 47 start-page: 8340 year: 2011 ident: WOS:000292980900042 article-title: Chemoselectivity in the Cu-catalyzed O-arylation of phenols and aliphatic alcohols publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc12694f – volume: 74 start-page: 5476 year: 2009 ident: WOS:000268480300045 article-title: A Simple and Convenient Copper-Catalyzed Tandem Synthesis of Quinoline-2-carboxylates at Room Temperature publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo901101v – volume: 54 start-page: 8321 year: 2011 ident: WOS:000297946300009 article-title: Synthesis, Antimalarial Activity, and Structure-Activity Relationship of 7-(2-Phenoxyethoxy)-4(1H)-quinolones publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm200718m – volume: 134 start-page: 10773 year: 2012 ident: WOS:000305863900015 article-title: Copper-Catalyzed Alkene Arylation with Diaryliodonium Salts publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja3039807 – volume: 24 start-page: 2066 year: 2014 ident: WOS:000334337100007 article-title: Identification and optimization of indolo[2,3-c]quinoline inhibitors of IRAK4 publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2014.03.056 – volume: 20 start-page: 11101 year: 2014 ident: WOS:000340902800030 article-title: Ruthenium-Catalyzed Cycloadditions of 1-Haloalkynes with Nitrile Oxides and Organic Azides: Synthesis of 4-Haloisoxazoles and 5-Halotriazoles publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201402559 – volume: 43 start-page: 6485 year: 2002 ident: WOS:000177617300046 article-title: Cu(I)-catalyzed three component coupling protocol for the synthesis of quinoline derivatives publication-title: TETRAHEDRON LETTERS – volume: 56 start-page: 6871 year: 2013 ident: WOS:000330097400027 article-title: Exquisite Selectivity for Human Toll-Like Receptor 8 in Substituted Furo[2,3-c]quinolines publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm400694d – volume: 80 start-page: 4516 year: 2015 ident: WOS:000354004600029 article-title: Regioselective Synthesis of 3-Bromoquinoline Derivatives and Diastereoselective Synthesis of Tetrahydroquinolines via Acid-Promoted Rearrangement of Arylmethyl Azides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.5b00375 – volume: 17 start-page: 4136 year: 2015 ident: WOS:000361087200004 article-title: Utilization of Copper-Catalyzed Carboarylation-Ring Closure for the Synthesis of New Oxazoline Derivatives publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b01860 – volume: 323 start-page: 1593 year: 2009 ident: WOS:000264342300035 article-title: A Meta-Selective Copper-Catalyzed C-H Bond Arylation publication-title: SCIENCE doi: 10.1126/science.1169975 – volume: 75 start-page: 1266 year: 2010 ident: WOS:000274465700030 article-title: A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo902603v – volume: 7 start-page: 59 year: 1953 ident: WOS:A1953UZ71800002 article-title: THE SKRAUP SYNTHESIS OF QUINOLINES publication-title: ORGANIC REACTIONS – volume: 76 start-page: 5774 year: 2011 ident: WOS:000292480300026 article-title: 3-Haloquinolines by Friedlander Reaction of alpha-Haloketones publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo2008252 – volume: 68 start-page: 1161 year: 2014 ident: WOS:000346354200032 article-title: Quinoline: A promising antitubercular target publication-title: BIOMEDICINE & PHARMACOTHERAPY doi: 10.1016/j.biopha.2014.10.007 – volume: 12 start-page: 1116 year: 2008 ident: WOS:000259447100004 article-title: Advances in the syntheses of quinoline and quinoline-annulated ring systems publication-title: CURRENT ORGANIC CHEMISTRY – volume: 121 start-page: 8162 year: 2009 ident: 000382968100012.31 article-title: Copper (I) catalyzed cycloaddition of organic azides and 1 iodoalkynes publication-title: Angew. Chem. – volume: 255 start-page: 2514 year: 2011 ident: WOS:000295768600008 article-title: NIR-emissive erbium-quinolinolate complexes publication-title: COORDINATION CHEMISTRY REVIEWS doi: 10.1016/j.ccr.2011.01.013 – volume: 340 start-page: 457 year: 2013 ident: WOS:000318016700036 article-title: Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions publication-title: SCIENCE – volume: 57 start-page: 3884 year: 2014 ident: WOS:000335879100022 article-title: Syntheses, Radiolabelings, and in Vitro Evaluations of Fluorinated PET Radioligands of 5-HT6 Serotoninergic Receptors publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm500372e – volume: 5 start-page: 42020 year: 2015 ident: WOS:000354445900083 article-title: \ Metal-free domino one-pot protocols for quinoline synthesis publication-title: RSC ADVANCES doi: 10.1039/c5ra07798b – volume: 70 start-page: 130 year: 2013 ident: WOS:000330554400013 article-title: Structure-activity relationship (SAR) and preliminary mode of action studies of 3-substituted benzylthioquinolinium iodide as anti-opportunistic infection agents publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2013.09.044 – volume: 16 start-page: 3515 year: 2014 ident: WOS:000338298600016 article-title: Glycerol: a biorenewable solvent for base-free Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling publication-title: GREEN CHEMISTRY doi: 10.1039/c4gc00451e – volume: 66 start-page: 6040 year: 2010 ident: WOS:000280541800014 article-title: Synthesis of 1H-pyrrolo[3,2-c]quinoline derivatives via palladium-catalyzed heteroannulation of 2-aryl-3-iodo-4-(phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinolines publication-title: TETRAHEDRON doi: 10.1016/j.tet.2010.06.018 – volume: 252 start-page: 812 year: 2008 ident: WOS:000256005000002 article-title: 8-Hydroxyquinolines in metallosupramolecular chemistry publication-title: COORDINATION CHEMISTRY REVIEWS doi: 10.1016/j.ccr.2007.06.003
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Snippet	A novel method for the synthesis of 3‐iodoquinolines was developed by copper‐catalyzed tandem annulation from diaryliodoniums, nitriles, and 1‐iodoalkynes. It... A novel method for the synthesis of 3-iodoquinolines was developed by copper-catalyzed tandem annulation from diaryliodoniums, nitriles, and 1-iodoalkynes. It...
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SubjectTerms	1-iodoalkynes annulation Catalysis Chemical reactions Chemistry Chemistry, Applied Chemistry, Organic copper catalysts iodoniums Nitriles Organic chemistry Physical Sciences Science & Technology Synthesis synthesis of quinolones tandem reactions
Title	Synthesis of 3-Iodoquinolines by Copper-Catalyzed Tandem Annulation from Diaryliodoniums, Nitriles, and 1-Iodoalkynes
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