Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines

被引：145

作者：

Qin, Xurong ^{[1
]}

Lee, Marcus Wen Yao ^{[1
]}

Zhou, Jianrong Steve ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 41期

关键词：

asymmetric catalysis; cyclization; indolines; nickel; reductive Heck reaction; REDOX-RELAY STRATEGY; QUATERNARY STEREOCENTERS; CONJUGATE ADDITION; COUPLING REACTIONS; ALKENYL ALCOHOLS; ORGANIC HALIDES; CHIRAL LIGANDS; HYDRIDE SOURCE; PALLADIUM; OLEFINS;

D O I：

10.1002/anie.201707134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nickel-catalyzed asymmetric reductive Heck reaction of aryl chlorides has been developed that affords substituted indolines with high enantioselectivity. Manganese powder is used as the terminal reductant with water as a proton source. Mechanistically, it is distinct from the palladium-catalyzed process in that the nickel-carbon bond is converted into a C-H bond to release the product through protonation instead of hydride donation followed by C-H reductive elimination on Pd.

引用

页码：12723 / 12726

页数：4

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