Iron-Catalyzed Directed C2-Alkylation and Alkenylation of Indole with Vinylarenes and Alkynes

被引：99

作者：

Wong, Mun Yee ^{[1
]}

Yamakawa, Takeshi ^{[1
]}

Yoshikai, Naohiko ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 03期

基金：

新加坡国家研究基金会;

关键词：

C-H BOND; NICKEL/LEWIS ACID CATALYSIS; CROSS-COUPLING REACTIONS; CARBON-HYDROGEN BONDS; AROMATIC IMINES; ORTHO-ALKYLATION; SELECTIVE HYDROARYLATION; RUTHENIUM CATALYST; ACTIVATION; COBALT;

D O I：

10.1021/ol503395g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iron-N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C-H activation. The former reaction affords 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments suggest that these reactions involve oxidative addition of the C-H bond to the iron center, insertion of the unsaturated bond into the Fe-H bond, and C-C reductive elimination.

引用

页码：442 / 445

页数：4

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