Hydroarylation of Alkynes Catalyzed by Nickel

被引:198
作者
Nakao, Yoshiaki [1 ]
机构
[1] Kyoto Univ, Dept Chem Mat, Grad Sch Engn, Kyoto 6158510, Japan
关键词
alkynes; C-H functionalization; hydroarylation; Lewis acids; nickel; C-H BONDS; PYRIDINE-N-OXIDES; DIRECT ARYLATION; SELECTIVE ALKENYLATION; INTRAMOLECULAR ARYLCYANATION; CIS-ADDITION; ATOM ECONOMY; ACTIVATION; ARYL; CARBOCYANATION;
D O I
10.1002/tcr.201100023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Nickel catalysts derived from bis(1,5-cyclooctadiene) nickel [ Ni(cod)(2)] and trialkylphosphines effect hydroarylation of alkynes through functionalization of C-H bonds of arenes including benzo-fused five-membered heteroarenes, pyridine-N-oxides, pyridines, 2-pyridones, and perfluoroarenes. The reactions proceed with excellent stereo-and regioselectivity to give disubstituted arylethenes in good yields. Use of Lewis acid (LA) co-catalysts is crucial for success in reactions of imidazoles, pyridines, and 2-pyridones; it is possible that coordination of the LA to the nitrogen or oxygen functionalities of such substrates increases the reactivity of their C-H bonds towards nickel(0) species. DOI 10.1002/tcr.201100023
引用
收藏
页码:242 / 251
页数:10
相关论文
共 99 条
[1]   TRANSITION-METAL COMPLEXES OF DIAZENES .35. SYNTHESIS OF 1-(ARYLAMINO)INDOLES BY RODIUM-CATALYZED ADDITION OF ALKYNES TO 1,2-DIARYLDIAZENES [J].
AULWURM, UR ;
MELCHINGER, JU ;
KISCH, H .
ORGANOMETALLICS, 1995, 14 (07) :3385-3395
[2]   Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2009, 65 (50) :10269-10310
[3]   Carboxylation of C-H Bonds Using N-Heterocyclic Carbene Gold(I) Complexes [J].
Boogaerts, Ine I. F. ;
Nolan, Steven P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :8858-+
[4]  
Braun T, 1999, ANGEW CHEM INT EDIT, V38, P3326, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3326::AID-ANIE3326>3.0.CO
[5]  
2-7
[6]   Redox Economy in Organic Synthesis [J].
Burns, Noah Z. ;
Baran, Phil S. ;
Hoffmann, Reinhard W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867
[7]   A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].
Campeau, LC ;
Rousseaux, S ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021
[8]   Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].
Campeau, Louis-Charles ;
Stuart, David R. ;
Leclerc, Jean-Philippe ;
Bertrand-Laperle, Megan ;
Villemure, Elisia ;
Sun, Ho-Yan ;
Lasserre, Sandrine ;
Guimond, Nicolas ;
Lecavallier, Melanie ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306
[9]   Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates [J].
Canivet, Jerome ;
Yamaguchi, Junichiro ;
Ban, Ikuya ;
Itami, Kenichiro .
ORGANIC LETTERS, 2009, 11 (08) :1733-1736
[10]   RuCl3-Catalyzed Alkenylation of Aromatic C-H Bonds with Terminal Alkynes [J].
Cheng, Kai ;
Yao, Bangben ;
Zhao, Jinlong ;
Zhang, Yuhong .
ORGANIC LETTERS, 2008, 10 (22) :5309-5312