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
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