Phosphonium Salts as Pseudohalides: Regioselective Nickel‐Catalyzed Cross‐Coupling of Complex Pyridines and Diazines
Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross‐coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for sel...
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| Published in | Angewandte Chemie International Edition Vol. 56; no. 33; pp. 9833 - 9836 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
07.08.2017
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross‐coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross‐couplings compared to halides, enabling chemoselective palladium‐ and nickel‐catalyzed coupling sequences.
Pyridines and diazines can be selectively converted into heterocyclic phosphonium salts that function as generic alternatives to heteroaryl halides in a nickel‐catalyzed Suzuki–Miyaura coupling reaction. Complex pyridines, drug‐like fragments, and pharmaceuticals can be arylated according to this two‐step method. |
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| AbstractList | Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross-coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross-couplings compared to halides, enabling chemoselective palladium-and nickel-catalyzed coupling sequences. Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross-coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross-couplings compared to halides, enabling chemoselective palladium- and nickel-catalyzed coupling sequences.Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross-coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross-couplings compared to halides, enabling chemoselective palladium- and nickel-catalyzed coupling sequences. Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross‐coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross‐couplings compared to halides, enabling chemoselective palladium‐ and nickel‐catalyzed coupling sequences. Pyridines and diazines can be selectively converted into heterocyclic phosphonium salts that function as generic alternatives to heteroaryl halides in a nickel‐catalyzed Suzuki–Miyaura coupling reaction. Complex pyridines, drug‐like fragments, and pharmaceuticals can be arylated according to this two‐step method. |
| Author | Zhang, Xuan McNally, Andrew |
| Author_xml | – sequence: 1 givenname: Xuan surname: Zhang fullname: Zhang, Xuan organization: Colorado State University – sequence: 2 givenname: Andrew orcidid: 0000-0002-8651-1631 surname: McNally fullname: McNally, Andrew email: andy.mcnally@colostate.edu organization: Colorado State University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28636128$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ja5049303 10.1016/S0065-2725(08)60288-3 10.1002/anie.200904306 10.1002/ange.200503479 10.1002/anie.201207428 10.1021/ja034908b 10.1002/chem.201003039 10.1126/science.1259203 10.1021/jm200187y 10.1021/jo070341w 10.1002/chem.200903337 10.1246/cl.1995.1101 10.1002/ange.200904306 10.1021/acs.orglett.5b00766 10.1002/ange.201207428 10.1021/ja1073799 10.1002/9783527619535 10.1039/C5CS00628G 10.1002/9781118309872.ch2 10.1021/ja00431a028 10.1021/ja409076z 10.1021/ja412563e 10.1021/acscatal.5b00498 10.1021/jacs.6b08662 10.1002/ange.200600493 10.1002/anie.200501582 10.1039/C7SC00675F 10.1007/s00706-016-1883-7 10.1016/S0040-4039(00)96178-1 10.1021/ol060268g 10.1039/B616082D 10.1002/ange.200501582 10.1002/anie.200600493 10.1002/anie.200503479 10.1002/9783527619405 10.1021/ol401727y 10.1039/c5cs00628g 10.1039/c7sc00675f 10.1039/b616082d |
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| Keywords | MEDICINAL CHEMISTS TOOLBOX diazines pyridines phosphonium salts cross-coupling LATE-STAGE FUNCTIONALIZATION nickel catalysis |
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| References | 2017; 8 2010; 16 2015; 17 2015; 5 2012 2015; 347 2009 2009; 48 121 2006; 8 1995 2011; 54 2004 2007; 72 2011; 17 2014; 136 2007; 36 1976; 98 2006 2006; 45 118 1993; 58 2013; 15 2000 2012 2012; 51 124 2010; 132 2013; 135 2005 2005; 44 117 2016; 138 2003; 125 1987; 28 2017; 148 2016; 45 e_1_2_2_4_1 e_1_2_2_24_2 e_1_2_2_22_2 e_1_2_2_6_2 e_1_2_2_20_1 e_1_2_2_2_2 e_1_2_2_41_2 e_1_2_2_43_1 e_1_2_2_28_2 e_1_2_2_8_1 e_1_2_2_26_1 Joule J. A. (e_1_2_2_21_2) 2000 e_1_2_2_13_2 e_1_2_2_36_2 e_1_2_2_38_1 e_1_2_2_11_2 e_1_2_2_30_1 e_1_2_2_30_2 e_1_2_2_19_1 e_1_2_2_32_1 e_1_2_2_17_2 e_1_2_2_34_1 e_1_2_2_15_2 e_1_2_2_13_3 e_1_2_2_3_2 e_1_2_2_5_2 e_1_2_2_23_1 e_1_2_2_1_1 e_1_2_2_40_1 e_1_2_2_42_2 e_1_2_2_7_2 e_1_2_2_29_1 e_1_2_2_44_1 e_1_2_2_27_2 e_1_2_2_9_3 e_1_2_2_9_2 e_1_2_2_25_2 e_1_2_2_12_2 e_1_2_2_37_2 e_1_2_2_10_3 e_1_2_2_39_1 e_1_2_2_10_2 e_1_2_2_31_1 e_1_2_2_18_2 e_1_2_2_16_3 e_1_2_2_33_1 e_1_2_2_16_2 e_1_2_2_35_1 e_1_2_2_14_2 GRIMMETT, MR (WOS:A1993BA01G00006) 1993; 58 ANDERS, E (WOS:A1987H714600002) 1987; 28 Dowlut, M (WOS:000277208900019) 2010; 16 Blakey, SB (WOS:000182959600019) 2003; 125 Sakamoto, M (WOS:A1995TP52400017) 1995 (000406798700032.31) 1000 Guram, AS (WOS:000247612200010) 2007; 72 Shields, JD (WOS:000354004400033) 2015; 17 (000406798700032.9) 2004 Larsen, MA (WOS:000333435500031) 2014; 136 Roughley, SD (WOS:000290651800001) 2011; 54 Kinzel, T (WOS:000282660100042) 2010; 132 Guram, AS (WOS:000237174500010) 2006; 8 (000406798700032.25) 2006 Santanilla, AB (WOS:000347102300044) 2015; 347 Kudo, N (WOS:000235412800025) 2006; 45 Markovic, T (WOS:000402384900032) 2017; 8 Campeau, LC (WOS:000247341300004) 2007; 36 Joule, J. A. (000406798700032.22) 2000; 4th Zhao, DB (WOS:000290216000001) 2011; 17 (000406798700032.21) 2005 Billingsley, KL (WOS:000237980000019) 2006; 45 Ge, SZ (WOS:000312305400037) 2012; 51 FAHEY, DR (WOS:A1976BY49100028) 1976; 98 Magano, J (WOS:000354012200055) 2015; 5 Ramgren, SD (WOS:000322853000038) 2013; 15 Steib, AK (WOS:000326125200020) 2013; 135 Hilton, MC (WOS:000386540500011) 2016; 138 (000406798700032.4) 2006 (000406798700032.14) 2012 (000406798700032.29) 2009 (000406798700032.2) 2004 Fier, PS (WOS:000339228200055) 2014; 136 (000406798700032.8) 1000 Hwang, LK (WOS:000232287700011) 2005; 44 Dobrounig, P (WOS:000392400000002) 2017; 148 Molander, GA (WOS:000272500900009) 2009; 48 Cernak, T (WOS:000369532200007) 2016; 45 |
| References_xml | – volume: 72 start-page: 5104 year: 2007 publication-title: J. Org. Chem. – volume: 48 121 start-page: 9240 9404 year: 2009 2009 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 125 start-page: 6046 year: 2003 publication-title: J. Am. Chem. Soc. – volume: 45 118 start-page: 1282 1304 year: 2006 2006 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 51 124 start-page: 12837 13009 year: 2012 2012 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 17 start-page: 2166 year: 2015 publication-title: Org. Lett. – volume: 45 118 start-page: 3484 3564 year: 2006 2006 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 8 start-page: 1787 year: 2006 publication-title: Org. Lett. – volume: 347 start-page: 49 year: 2015 publication-title: Science – volume: 45 start-page: 546 year: 2016 publication-title: Chem. Soc. Rev. – volume: 16 start-page: 4279 year: 2010 publication-title: Chem. Eur. J. – year: 2000 – start-page: 25 year: 2012 end-page: 96 – volume: 17 start-page: 5466 year: 2011 publication-title: Chem. Eur. J. – start-page: 1101 year: 1995 end-page: 1102 publication-title: Chem. Lett. – volume: 135 start-page: 15346 year: 2013 publication-title: J. Am. Chem. Soc. – volume: 8 start-page: 4437 year: 2017 publication-title: Chem. Sci. – volume: 132 start-page: 14073 year: 2010 publication-title: J. Am. Chem. Soc. – volume: 28 start-page: 2675 year: 1987 publication-title: Tetrahedron Lett. – volume: 54 start-page: 3451 year: 2011 publication-title: J. Med. Chem. – volume: 138 start-page: 13806 year: 2016 publication-title: J. Am. Chem. Soc. – volume: 15 start-page: 3950 year: 2013 publication-title: Org. Lett. – year: 2004 – volume: 136 start-page: 4287 year: 2014 publication-title: J. Am. Chem. Soc. – volume: 148 start-page: 3 year: 2017 publication-title: Monatsh. Chem. – volume: 136 start-page: 10139 year: 2014 publication-title: J. Am. Chem. Soc. – volume: 44 117 start-page: 6166 6322 year: 2005 2005 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 5 start-page: 3120 year: 2015 publication-title: ACS Catal. – volume: 98 start-page: 4499 year: 1976 publication-title: J. Am. Chem. Soc. – volume: 36 start-page: 1058 year: 2007 publication-title: Chem. Soc. Rev. – volume: 58 start-page: 271 year: 1993 end-page: 329 publication-title: Adv. Heterocycl. Chem. – ident: e_1_2_2_19_1 doi: 10.1021/ja5049303 – volume-title: Heterocyclic Chemistry year: 2000 ident: e_1_2_2_21_2 – ident: e_1_2_2_22_2 doi: 10.1016/S0065-2725(08)60288-3 – ident: e_1_2_2_40_1 – ident: e_1_2_2_38_1 – ident: e_1_2_2_13_2 doi: 10.1002/anie.200904306 – ident: e_1_2_2_10_3 doi: 10.1002/ange.200503479 – ident: e_1_2_2_23_1 – ident: e_1_2_2_16_2 doi: 10.1002/anie.201207428 – ident: e_1_2_2_29_1 doi: 10.1021/ja034908b – ident: e_1_2_2_3_2 doi: 10.1002/chem.201003039 – ident: e_1_2_2_4_1 – ident: e_1_2_2_33_1 doi: 10.1126/science.1259203 – ident: e_1_2_2_32_1 doi: 10.1021/jm200187y – ident: e_1_2_2_12_2 doi: 10.1021/jo070341w – ident: e_1_2_2_14_2 doi: 10.1002/chem.200903337 – ident: e_1_2_2_31_1 doi: 10.1246/cl.1995.1101 – ident: e_1_2_2_13_3 doi: 10.1002/ange.200904306 – ident: e_1_2_2_41_2 doi: 10.1021/acs.orglett.5b00766 – ident: e_1_2_2_16_3 doi: 10.1002/ange.201207428 – ident: e_1_2_2_15_2 doi: 10.1021/ja1073799 – ident: e_1_2_2_44_1 – ident: e_1_2_2_6_2 doi: 10.1002/9783527619535 – ident: e_1_2_2_1_1 – ident: e_1_2_2_39_1 doi: 10.1039/C5CS00628G – ident: e_1_2_2_7_2 doi: 10.1002/9781118309872.ch2 – ident: e_1_2_2_35_1 – ident: e_1_2_2_37_2 doi: 10.1021/ja00431a028 – ident: e_1_2_2_17_2 doi: 10.1021/ja409076z – ident: e_1_2_2_25_2 doi: 10.1021/ja412563e – ident: e_1_2_2_42_2 doi: 10.1021/acscatal.5b00498 – ident: e_1_2_2_20_1 – ident: e_1_2_2_27_2 doi: 10.1021/jacs.6b08662 – ident: e_1_2_2_9_3 doi: 10.1002/ange.200600493 – ident: e_1_2_2_30_1 doi: 10.1002/anie.200501582 – ident: e_1_2_2_34_1 – ident: e_1_2_2_26_1 – ident: e_1_2_2_24_2 doi: 10.1039/C7SC00675F – ident: e_1_2_2_43_1 doi: 10.1007/s00706-016-1883-7 – ident: e_1_2_2_28_2 doi: 10.1016/S0040-4039(00)96178-1 – ident: e_1_2_2_11_2 doi: 10.1021/ol060268g – ident: e_1_2_2_2_2 doi: 10.1039/B616082D – ident: e_1_2_2_8_1 – ident: e_1_2_2_36_2 doi: 10.1016/S0040-4039(00)96178-1 – ident: e_1_2_2_30_2 doi: 10.1002/ange.200501582 – ident: e_1_2_2_9_2 doi: 10.1002/anie.200600493 – ident: e_1_2_2_10_2 doi: 10.1002/anie.200503479 – ident: e_1_2_2_5_2 doi: 10.1002/9783527619405 – ident: e_1_2_2_18_2 doi: 10.1021/ol401727y – volume: 8 start-page: 1787 year: 2006 ident: WOS:000237174500010 article-title: New air-stable catalysts for general and efficient Suzuki-Miyaura cross-coupling reactions of heteroaryl chlorides publication-title: ORGANIC LETTERS doi: 10.1021/ol060268g – volume: 136 start-page: 10139 year: 2014 ident: WOS:000339228200055 article-title: Synthesis and Late-Stage Functionalization of Complex Molecules through C-H Fluorination and Nucleophilic Aromatic Substitution publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja5049303 – year: 2006 ident: 000406798700032.25 publication-title: ANGEW CHEM INT EDIT – volume: 51 start-page: 12837 year: 2012 ident: WOS:000312305400037 article-title: Highly Reactive, Single-Component Nickel Catalyst Precursor for Suzuki-Miyuara Cross-Coupling of Heteroaryl Boronic Acids with Heteroaryl Halides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201207428 – year: 2004 ident: 000406798700032.9 publication-title: METAL CATALYZED CROS – volume: 45 start-page: 3484 year: 2006 ident: WOS:000237980000019 article-title: A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200600493 – volume: 347 start-page: 49 year: 2015 ident: WOS:000347102300044 article-title: Nanomole-scale high-throughput chemistry for the synthesis of complex molecules publication-title: SCIENCE doi: 10.1126/science.1259203 – year: 2004 ident: 000406798700032.2 publication-title: TRANSITION METALS OR – volume: 17 start-page: 5466 year: 2011 ident: WOS:000290216000001 article-title: Recent Progress in Coupling of Two Heteroarenes publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201003039 – year: 2009 ident: 000406798700032.29 publication-title: ANGEW – year: 2006 ident: 000406798700032.4 publication-title: ANGEW CHEM INT EDIT – year: 2012 ident: 000406798700032.14 publication-title: ANGEW CHEM – volume: 44 start-page: 6166 year: 2005 ident: WOS:000232287700011 article-title: Tetraarylphosphonium halides as arylating reagents in Pd-catalyzed Heck and cross-coupling reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200501582 – year: 1000 ident: 000406798700032.8 publication-title: APPL TRANSITION META – volume: 58 start-page: 271 year: 1993 ident: WOS:A1993BA01G00006 article-title: HALOGENATION OF HETEROCYCLES .2. 6-MEMBERED AND 7-MEMBERED RINGS publication-title: ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 58 – volume: 138 start-page: 13806 year: 2016 ident: WOS:000386540500011 article-title: Selective Functionalization of Pyridines via Heterocyclic Phosphonium Salts publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b08662 – volume: 48 start-page: 9240 year: 2009 ident: WOS:000272500900009 article-title: Organotrifluoroborates and Monocoordinated Palladium Complexes as Catalysts-A Perfect Combination for Suzuki-Miyaura Coupling publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200904306 – volume: 16 start-page: 4279 year: 2010 ident: WOS:000277208900019 article-title: An Efficient Low-Temperature Stille-Migita Cross-Coupling Reaction for Heteroaromatic Compounds by Pd-PEPPSI-IPent publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200903337 – volume: 5 start-page: 3120 year: 2015 ident: WOS:000354012200055 article-title: Development of an Air-Stable, Broadly Applicable Nickel Source for Nickel-Catalyzed Cross-Coupling publication-title: ACS CATALYSIS doi: 10.1021/acscatal.5b00498 – volume: 136 start-page: 4287 year: 2014 ident: WOS:000333435500031 article-title: Iridium-Catalyzed C-H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja412563e – volume: 98 start-page: 4499 year: 1976 ident: WOS:A1976BY49100028 article-title: REVERSIBLE OXIDATIVE ADDITION OF TRIPHENYLPHOSPHINE TO ZERO-VALENT NICKEL AND PALLADIUM COMPLEXES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 132 start-page: 14073 year: 2010 ident: WOS:000282660100042 article-title: A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja1073799 – volume: 17 start-page: 2166 year: 2015 ident: WOS:000354004400033 article-title: A Modular, Air-Stable Nickel Precatalyst publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b00766 – volume: 15 start-page: 3950 year: 2013 ident: WOS:000322853000038 article-title: Nickel-Catalyzed Suzuki-Miyaura Couplings in Green Solvents publication-title: ORGANIC LETTERS doi: 10.1021/ol401727y – volume: 28 start-page: 2675 year: 1987 ident: WOS:A1987H714600002 article-title: NEW METHODS FOR REGIOSPECIFIC SUBSTITUTION OF SLOW-REACTING N-HETEROAROMATIC RING-SYSTEMS publication-title: TETRAHEDRON LETTERS – volume: 135 start-page: 15346 year: 2013 ident: WOS:000326125200020 article-title: Efficient Chromium(II)-Catalyzed Cross-Coupling Reactions between Csp2 Centers publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja409076z – volume: 54 start-page: 3451 year: 2011 ident: WOS:000290651800001 article-title: The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm200187y – volume: 45 start-page: 546 year: 2016 ident: WOS:000369532200007 article-title: The medicinal chemist's toolbox for late stage functionalization of drug-like molecules publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c5cs00628g – volume: 8 start-page: 4437 year: 2017 ident: WOS:000402384900032 article-title: Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides publication-title: CHEMICAL SCIENCE doi: 10.1039/c7sc00675f – volume: 36 start-page: 1058 year: 2007 ident: WOS:000247341300004 article-title: Applications of and alternatives to π-electron-deficient azine organometallics in metal catalyzed cross-coupling reactions publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b616082d – volume: 125 start-page: 6046 year: 2003 ident: WOS:000182959600019 article-title: The first Suzuki cross-couplings of aryltrimethylammonium salts publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034908b – year: 2005 ident: 000406798700032.21 publication-title: ANGEW CHEM – volume: 72 start-page: 5104 year: 2007 ident: WOS:000247612200010 article-title: New catalysts for Suzuki-Miyaura coupling reactions of heteroatom-substituted heteroaryl chlorides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo070341w – volume: 45 start-page: 1282 year: 2006 ident: WOS:000235412800025 article-title: A versatile method for Suzuki cross-coupling reactions of nitrogen heterocycles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200503479 – volume: 4th year: 2000 ident: 000406798700032.22 publication-title: Heterocyclic Chemistry – start-page: 1101 year: 1995 ident: WOS:A1995TP52400017 article-title: Palladium-catalyzed cleavage of P-C bonds in quaternary phosphonium salts and its applications to organic synthesis publication-title: CHEMISTRY LETTERS – year: 1000 ident: 000406798700032.31 publication-title: TETRAHEDRON LETT – volume: 148 start-page: 3 year: 2017 ident: WOS:000392400000002 article-title: Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis publication-title: MONATSHEFTE FUR CHEMIE doi: 10.1007/s00706-016-1883-7 |
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| Snippet | Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross‐coupling methods. An alternative approach is presented where... Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross-coupling methods. An alternative approach is presented where... |
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| SubjectTerms | Aromatic compounds Catalysts Chemistry Chemistry, Multidisciplinary Coupling methods Couplings Cross coupling diazines Halides Nickel nickel catalysis Palladium Pharmacology Pharmacophores phosphonium salts Physical Sciences Pyridines Regioselectivity Salts Science & Technology |
| Title | Phosphonium Salts as Pseudohalides: Regioselective Nickel‐Catalyzed Cross‐Coupling of Complex Pyridines and Diazines |
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