Mizoroki-Heck-Type Reaction Mediated by Potassium tert-Butoxide
In the absence of transition‐metal catalysts, a Mizoroki–Heck‐type reaction proceeded to give stilbene derivatives in a simple manner using an aryl halide, a styrene derivative, KOtBu, EtOH, and DMF (see scheme; DMF=N,N‐dimethylformamide).
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Published in | Angewandte Chemie (International ed.) Vol. 50; no. 20; pp. 4671 - 4674 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
09.05.2011
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Abstract | In the absence of transition‐metal catalysts, a Mizoroki–Heck‐type reaction proceeded to give stilbene derivatives in a simple manner using an aryl halide, a styrene derivative, KOtBu, EtOH, and DMF (see scheme; DMF=N,N‐dimethylformamide). |
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AbstractList | In the absence of transition‐metal catalysts, a Mizoroki–Heck‐type reaction proceeded to give stilbene derivatives in a simple manner using an aryl halide, a styrene derivative, KOtBu, EtOH, and DMF (see scheme; DMF=N,N‐dimethylformamide). |
Author | Zhang, Xuejing Hayashi, Tamio Shirakawa, Eiji |
Author_xml | – sequence: 1 givenname: Eiji surname: Shirakawa fullname: Shirakawa, Eiji email: shirakawa@kuchem.kyoto-u.ac.jp organization: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 (Japan), Fax: (+81) 75-753-3988 – sequence: 2 givenname: Xuejing surname: Zhang fullname: Zhang, Xuejing organization: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 (Japan), Fax: (+81) 75-753-3988 – sequence: 3 givenname: Tamio surname: Hayashi fullname: Hayashi, Tamio organization: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502 (Japan), Fax: (+81) 75-753-3988 |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21472936$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1021/ja1080822 10.1038/NCHEM.862 10.1039/b302683c 10.1021/ja103050x 10.1021/cr9903048 10.1021/ol8019764 10.1016/S0040-4039(01)81536-7 10.1021/ja00188a069 10.1021/ja00015a025 10.1038/nchem.862 10.1016/S0040-4039(00)88160-5 10.1021/ja01012a026 10.1002/9783527618293.ch29 10.1002/9780470716076.ch10 10.1002/9783527619535.ch5 10.1039/cs9861500261 10.1021/ar50131a003 10.1002/chem.200801306 10.1021/jo000669o 10.1021/ja00015a024 10.1002/0471212466.ch46 10.1021/jo00324a056 10.1021/jo00369a008 |
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Keywords | C-C coupling HALIDES SINGLE ELECTRON-TRANSFER REDUCTION HYDROCARBONS ALKOXIDES aryl radicals ARYLATION single-electron transfer alkenes synthetic methods |
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Notes | ark:/67375/WNG-TBW3CTWH-D This work was supported financially by a Grant-in-Aid for Scientific Research (the Global COE Program "Integrated Materials Science" on Kyoto University) from Ministry of Education, Culture, Sports, Science and Technology (Japan). We are grateful to Ms. Yuki Yamamoto, Dr. Kenji Kitayama, and Mr. Ikuo Takahashi (Daicel Chemical Industries, Ltd.) for ICP analysis. We thank Dr. Kazufumi Kohno (Tokyo University of Agriculture and Technology) for carrying out duplicate experiments. Ministry of Education, Culture, Sports, Science and Technology (Japan) istex:25B6FCB65ABB8D342F4BD05DA25FFE4EC9025596 ArticleID:ANIE201008220 This work was supported financially by a Grant‐in‐Aid for Scientific Research (the Global COE Program “Integrated Materials Science” on Kyoto University) from Ministry of Education, Culture, Sports, Science and Technology (Japan). We are grateful to Ms. Yuki Yamamoto, Dr. Kenji Kitayama, and Mr. Ikuo Takahashi (Daicel Chemical Industries, Ltd.) for ICP analysis. We thank Dr. Kazufumi Kohno (Tokyo University of Agriculture and Technology) for carrying out duplicate experiments. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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References | J. W. Sease, F. G. Burton, S. L. Nickol, J. Am. Chem. Soc. 1968, 90, 2595-2598 S. Braese, A. de Meijere in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, pp. 217-315 E. C. Ashby, A. B. Goel, R. N. DePriest, J. Org. Chem. 1981, 46, 2429-2431 E. C. Ashby, D.-H. Bae, W.-S. Park, R. N. Depriest, W.-Y. Su, Tetrahedron Lett. 1984, 25, 5107-5110 S. Yanagisawa, K. Ueda, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 4673-4676 W. Liu, H. Cao, H. Zhang, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y. Kwong, A. Lei, J. Am. Chem. Soc. 2010, 132, 16737-16740 The coupling of iodobenzene with styrene in the absence of any transition-metal catalysts is reported to take place at a high temperature and a high pressure in supercritical water, thus giving stilbene in a moderate yield. R. Zhang, F. Zhao, M. Sato, Y. Ikushima, Chem. Commun. 2003, 1548-1549. J. F. Bunnett, Acc. Chem. Res. 1978, 11, 413-420. See also Ref. [3b]. A. Ogawa, I. Ogawa, N. Sonoda, J. Org. Chem. 2000, 65, 7682-7685. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066 C.-L. Sun, H. Li, D.-G. Yu, M. Yu, X. Zhou, X.-Y. Lu, K. Huang, S.-F. Zheng, B.-J. Li, Z.-J. Shi, Nat. Chem. 2010, 2, 1044-1049. We have reported that coupling of aryl halides with arenes mediated by NaOtBu proceeds through a homolytic aromatic substitution pathway, where a catalytic amount of a phenanthroline derivative is essential for generation of the aryl radical from aryl halides K. Meerholz, J. Heinze, J. Am. Chem. Soc. 1989, 111, 2325-2326 C. G. Screttas, M. Micha-Screttas, C. T. Cazianis, Tetrahedron Lett. 1983, 24, 3287-3288 J. Grimshaw, Electrochemical Reactions and Mechanisms in Organic Chemistry, Elsevier, Amsterdam, 2000, pp. 54-56, pp. 122-126, and pp. 239-243. E. Shirakawa, K. Itoh, T. Higashino, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 15537-15539. For a discussion on the mechanism of these reactions, see V. W. Bowry, J. Lusztyk, K. U. Ingold, J. Am. Chem. Soc. 1991, 113, 5687-5698 R. Bolton, G. H. Williams, Chem. Soc. Rev. 1986, 15, 261-289 For a recent review, see: M. R. Heinrich, Chem. Eur. J. 2009, 15, 820-833. V. W. Bowry, K. U. Ingold, J. Am. Chem. Soc. 1991, 113, 5699-5707 The Mizoroki-Heck reaction catalyzed by a metal other than palladium is also known but is rare. For a review, see: L. Ackermann, R. Born in Mizoroki-Heck Reaction (Ed.: M. Oestreich), Wiley, Chichester, 2009, pp. 383-403. E. C. Ashby, J. N. Argyropoulos, J. Org. Chem. 1986, 51, 3593-3597. 1991; 113 1986; 51 2001 1984; 25 1978; 11 2000 2000; 65 1986; 15 1989; 111 2009 2010; 132 1981; 46 1995 2008; 10 1968; 90 2004 2000; 100 2003 2002 2010; 2 1983; 24 2009; 15 ASHBY, EC (WOS:A1984TR47100001) 1984; 25 Studer, A. (000290663600022.21) 2001; 2 Studer, A. (000290663600022.22) 2011 Grimshaw, J. (000290663600022.12) 2000 BOLTON, R (WOS:A1986D363400006) 1986; 15 Fossey, J. (000290663600022.11) 1995 Larhed, M. (000290663600022.14) 2002; 1 ASHBY, EC (WOS:A1981LR08800056) 1981; 46 Liu, W (WOS:000284972400005) 2010; 132 Beletskaya, IP (WOS:000088838500011) 2000; 100 SCRETTAS, CG (WOS:A1983RB68000039) 1983; 24 BOWRY, VW (WOS:A1991FX87800025) 1991; 113 Braese, S. (000290663600022.9) 2004 Ogawa, A (WOS:000165203000055) 2000; 65 BUNNETT, JF (WOS:A1978FW00900003) 1978; 11 Shirakawa, E (WOS:000283955600027) 2010; 132 Ackermann, L. (000290663600022.1) 2009 BOWRY, VW (WOS:A1991FX87800024) 1991; 113 Yanagisawa, S (WOS:000259940600071) 2008; 10 ASHBY, EC (WOS:A1986E113800008) 1986; 51 Heinrich, MR (WOS:000262886800001) 2009; 15 MEERHOLZ, K (WOS:A1989T780200069) 1989; 111 Sun, CL (WOS:000284527300012) 2010; 2 Zhang, R (WOS:000183482500038) 2003 SEASE, JW (WOS:A1968B064900027) 1968; 90 e_1_2_2_3_2 e_1_2_2_24_2 e_1_2_2_4_2 e_1_2_2_23_2 e_1_2_2_5_2 e_1_2_2_22_2 e_1_2_2_6_2 e_1_2_2_21_2 e_1_2_2_20_2 e_1_2_2_1_2 e_1_2_2_2_2 Fossey J. (e_1_2_2_8_2) 1995 e_1_2_2_29_2 e_1_2_2_7_2 e_1_2_2_28_2 e_1_2_2_27_2 e_1_2_2_26_2 e_1_2_2_9_2 e_1_2_2_25_2 Grimshaw J. (e_1_2_2_32_2) 2000 e_1_2_2_13_2 e_1_2_2_36_2 e_1_2_2_12_2 e_1_2_2_11_2 e_1_2_2_10_2 e_1_2_2_19_2 e_1_2_2_30_2 e_1_2_2_18_2 e_1_2_2_31_2 e_1_2_2_17_2 e_1_2_2_16_2 e_1_2_2_33_2 e_1_2_2_15_2 e_1_2_2_34_2 e_1_2_2_14_2 e_1_2_2_35_2 |
References_xml | – volume: 132 start-page: 15537 year: 2010 end-page: 15539 publication-title: J. Am. Chem. Soc. – volume: 11 start-page: 413 year: 1978 end-page: 420 publication-title: Acc. Chem. Res. – volume: 90 start-page: 2595 year: 1968 end-page: 2598 publication-title: J. Am. Chem. Soc. – volume: 113 start-page: 5699 year: 1991 end-page: 5707 publication-title: J. Am. Chem. Soc. – start-page: 217 year: 2004 end-page: 315 – volume: 25 start-page: 5107 year: 1984 end-page: 5110 publication-title: Tetrahedron Lett. – volume: 113 start-page: 5687 year: 1991 end-page: 5698 publication-title: J. Am. Chem. Soc. – volume: 10 start-page: 4673 year: 2008 end-page: 4676 publication-title: Org. Lett. – volume: 132 start-page: 16737 year: 2010 end-page: 16740 publication-title: J. Am. Chem. Soc. – volume: 46 start-page: 2429 year: 1981 end-page: 2431 publication-title: J. Org. Chem. – volume: 65 start-page: 7682 year: 2000 end-page: 7685 publication-title: J. Org. Chem. – start-page: 383 year: 2009 end-page: 403 – year: 2000 – volume: 2 start-page: 1044 year: 2010 end-page: 1049 publication-title: Nat. Chem. – volume: 111 start-page: 2325 year: 1989 end-page: 2326 publication-title: J. Am. Chem. Soc. – start-page: 166 year: 1995 end-page: 180 – volume: 24 start-page: 3287 year: 1983 end-page: 3288 publication-title: Tetrahedron Lett. – volume: 100 start-page: 3009 year: 2000 end-page: 3066 publication-title: Chem. Rev. – start-page: 1133 year: 2002 end-page: 1178 – start-page: 62 year: 2001 end-page: 80 – volume: 15 start-page: 820 year: 2009 end-page: 833 publication-title: Chem. Eur. J. – volume: 15 start-page: 261 year: 1986 end-page: 289 publication-title: Chem. Soc. Rev. – start-page: 1548 year: 2003 end-page: 1549 publication-title: Chem. Commun. – volume: 51 start-page: 3593 year: 1986 end-page: 3597 publication-title: J. Org. Chem. – volume: 111 start-page: 2325 year: 1989 ident: WOS:A1989T780200069 article-title: MULTIPLE REVERSIBLE ELECTROCHEMICAL REDUCTION OF AROMATIC-HYDROCARBONS IN LIQUID ALKYLAMINES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MEERHOLZ, K – volume: 1 start-page: 1133 year: 2002 ident: 000290663600022.14 publication-title: Handbook of Organopalladium Chemistry for Organic Synthesis contributor: fullname: Larhed, M. – volume: 25 start-page: 5107 year: 1984 ident: WOS:A1984TR47100001 article-title: EVIDENCE FOR SINGLE ELECTRON-TRANSFER IN THE REACTION OF ALKOXIDES WITH ALKYL-HALIDES publication-title: TETRAHEDRON LETTERS contributor: fullname: ASHBY, EC – start-page: 217 year: 2004 ident: 000290663600022.9 publication-title: Metal-Catalyzed Cross-Coupling Reactions contributor: fullname: Braese, S. – volume: 51 start-page: 3593 year: 1986 ident: WOS:A1986E113800008 article-title: SINGLE ELECTRON-TRANSFER IN THE MEERWEIN-PONNDORF-VERLEY REDUCTION OF BENZOPHENONE BY LITHIUM ALKOXIDES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ASHBY, EC – volume: 132 start-page: 15537 year: 2010 ident: WOS:000283955600027 article-title: tert-Butoxide-Mediated Arylation of Benzene with Aryl Halides in the Presence of a Catalytic 1,10-Phenanthroline Derivative publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja1080822 contributor: fullname: Shirakawa, E – volume: 113 start-page: 5687 year: 1991 ident: WOS:A1991FX87800024 article-title: CALIBRATION OF A NEW HOROLOGERY OF FAST RADICAL CLOCKS - RING-OPENING RATES FOR RING-ALKYL-SUBSTITUTED AND ALPHA-ALKYL-SUBSTITUTED CYCLOPROPYLCARBINYL RADICALS AND FOR THE BICYCLO[2.1.0]PENT-2-YL RADICAL publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BOWRY, VW – volume: 2 start-page: 1044 year: 2010 ident: WOS:000284527300012 article-title: An efficient organocatalytic method for constructing biaryls through aromatic C-H activation publication-title: NATURE CHEMISTRY doi: 10.1038/NCHEM.862 contributor: fullname: Sun, CL – volume: 24 start-page: 3287 year: 1983 ident: WOS:A1983RB68000039 article-title: THE BENZILIC ESTER REARRANGEMENT - EVIDENCE FOR A SET PATHWAY IN THE BENZILIC ESTER AND-OR ACID REARRANGEMENT publication-title: TETRAHEDRON LETTERS contributor: fullname: SCRETTAS, CG – start-page: 54 year: 2000 ident: 000290663600022.12 publication-title: Electrochemical Reactions and Mechanisms in Organic Chemistry contributor: fullname: Grimshaw, J. – volume: 113 start-page: 5699 year: 1991 ident: WOS:A1991FX87800025 article-title: A RADICAL CLOCK INVESTIGATION OF MICROSOMAL CYTOCHROME-P-450 HYDROXYLATION OF HYDROCARBONS - RATE OF OXYGEN REBOUND publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BOWRY, VW – volume: 2 start-page: 62 year: 2001 ident: 000290663600022.21 publication-title: Radicals in Organic Synthesis contributor: fullname: Studer, A. – volume: 46 start-page: 2429 year: 1981 ident: WOS:A1981LR08800056 article-title: EVIDENCE FOR SINGLE ELECTRON-TRANSFER IN THE REACTIONS OF ALKALI-METAL AMIDES AND ALKOXIDES WITH ALKYL-HALIDES AND POLYNUCLEAR HYDROCARBONS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ASHBY, EC – start-page: 1548 year: 2003 ident: WOS:000183482500038 article-title: Noncatalytic Heck coupling reaction using supercritical water publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b302683c contributor: fullname: Zhang, R – start-page: 166 year: 1995 ident: 000290663600022.11 publication-title: Free Radicals in Organic Chemistry contributor: fullname: Fossey, J. – volume: 11 start-page: 413 year: 1978 ident: WOS:A1978FW00900003 article-title: AROMATIC-SUBSTITUTION BY SRN1 MECHANISM publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: BUNNETT, JF – volume: 132 start-page: 16737 year: 2010 ident: WOS:000284972400005 article-title: Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C-H Arylation of Unactivated Benzene publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja103050x contributor: fullname: Liu, W – start-page: 383 year: 2009 ident: 000290663600022.1 publication-title: Mizoroki-Heck Reaction contributor: fullname: Ackermann, L. – volume: 90 start-page: 2595 year: 1968 ident: WOS:A1968B064900027 article-title: ON MECHANISM OF ELECTROLYTIC REDUCTION OF CARBON-HALOGEN BOND .2. A RHOSIGMA STUDY publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: SEASE, JW – volume: 100 start-page: 3009 year: 2000 ident: WOS:000088838500011 article-title: The heck reaction as a sharpening stone of palladium catalysis publication-title: CHEMICAL REVIEWS doi: 10.1021/cr9903048 contributor: fullname: Beletskaya, IP – volume: 15 start-page: 821 year: 2009 ident: WOS:000262886800001 article-title: Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts publication-title: CHEMISTRY-A EUROPEAN JOURNAL contributor: fullname: Heinrich, MR – volume: 10 start-page: 4673 year: 2008 ident: WOS:000259940600071 article-title: Potassium t-Butoxide Alone Can Promote the Biaryl Coupling of Electron-Deficient Nitrogen Heterocycles and Haloarenes publication-title: ORGANIC LETTERS doi: 10.1021/ol8019764 contributor: fullname: Yanagisawa, S – year: 2011 ident: 000290663600022.22 publication-title: Angew. Chem. contributor: fullname: Studer, A. – volume: 15 start-page: 261 year: 1986 ident: WOS:A1986D363400006 article-title: HOMOLYTIC ARYLATION OF AROMATIC AND POLYFLUOROAROMATIC COMPOUNDS publication-title: CHEMICAL SOCIETY REVIEWS contributor: fullname: BOLTON, R – volume: 65 start-page: 7682 year: 2000 ident: WOS:000165203000055 article-title: A novel three-component coupling of alkynes, vinylcyclopropanes, and diphenyl diselenide under visible-light irradiation publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Ogawa, A – start-page: 166 volume-title: Free Radicals in Organic Chemistry year: 1995 ident: e_1_2_2_8_2 contributor: fullname: Fossey J. – ident: e_1_2_2_11_2 – ident: e_1_2_2_28_2 – ident: e_1_2_2_26_2 doi: 10.1016/S0040-4039(01)81536-7 – ident: e_1_2_2_31_2 doi: 10.1021/ja00188a069 – ident: e_1_2_2_33_2 – volume-title: Electrochemical Reactions and Mechanisms in Organic Chemistry year: 2000 ident: e_1_2_2_32_2 contributor: fullname: Grimshaw J. – ident: e_1_2_2_15_2 doi: 10.1021/ja1080822 – ident: e_1_2_2_19_2 – ident: e_1_2_2_35_2 doi: 10.1021/ja00015a025 – ident: e_1_2_2_6_2 – ident: e_1_2_2_16_2 – ident: e_1_2_2_14_2 doi: 10.1038/nchem.862 – ident: e_1_2_2_25_2 doi: 10.1016/S0040-4039(00)88160-5 – ident: e_1_2_2_21_2 – ident: e_1_2_2_30_2 doi: 10.1021/ja01012a026 – ident: e_1_2_2_9_2 doi: 10.1002/9783527618293.ch29 – ident: e_1_2_2_2_2 doi: 10.1021/cr9903048 – ident: e_1_2_2_5_2 doi: 10.1002/9780470716076.ch10 – ident: e_1_2_2_1_2 – ident: e_1_2_2_3_2 doi: 10.1002/9783527619535.ch5 – ident: e_1_2_2_7_2 doi: 10.1039/cs9861500261 – ident: e_1_2_2_17_2 doi: 10.1039/b302683c – ident: e_1_2_2_22_2 doi: 10.1021/ar50131a003 – ident: e_1_2_2_10_2 doi: 10.1002/chem.200801306 – ident: e_1_2_2_36_2 doi: 10.1021/jo000669o – ident: e_1_2_2_13_2 doi: 10.1021/ja103050x – ident: e_1_2_2_20_2 – ident: e_1_2_2_29_2 – ident: e_1_2_2_34_2 doi: 10.1021/ja00015a024 – ident: e_1_2_2_4_2 doi: 10.1002/0471212466.ch46 – ident: e_1_2_2_24_2 doi: 10.1021/jo00324a056 – ident: e_1_2_2_12_2 doi: 10.1021/ol8019764 – ident: e_1_2_2_23_2 – ident: e_1_2_2_27_2 doi: 10.1021/jo00369a008 – ident: e_1_2_2_18_2 |
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Snippet | In the absence of transition‐metal catalysts, a Mizoroki–Heck‐type reaction proceeded to give stilbene derivatives in a simple manner using an aryl halide, a... |
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SubjectTerms | alkenes aryl radicals Butanols - chemistry Chemistry Chemistry, Multidisciplinary CC coupling Molecular Structure Physical Sciences Science & Technology single-electron transfer Stereoisomerism Styrene - chemical synthesis Styrene - chemistry synthetic methods Toluene - analogs & derivatives Toluene - chemistry |
Title | Mizoroki-Heck-Type Reaction Mediated by Potassium tert-Butoxide |
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