Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Cross‐Coupling Reaction for the Stereoselective Synthesis of Multisubstituted Olefins

Author:

Wang Cui‐Tian1,Liang Peng‐Yu1,Li Ming2,Wang Bin1,Wang Yu‐Zhao1,Li Xue‐Song1,Wei Wan‐Xu1,Gou Xue‐Ya1,Ding Ya‐Nan1,Zhang Zhe1,Li Yu‐Ke3,Liu Xue‐Yuan1,Liang Yong‐Min1ORCID

Affiliation:

1. State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering Lanzhou University Lanzhou 730000 P. R. China

2. College of Chemistry and Chemical Engineering Northwest Normal University Lanzhou Gansu 730070 P. R. China

3. Department of Chemistry and Centre for Scientific Modeling and Computation Chinese University of Hong Kong Hong Kong China

Abstract

AbstractThe aryl‐to‐vinyl nickel 1,4‐migration (1,4‐Ni migration) reaction has been reported for the first time. The generated alkenyl Ni species undergo a reductive coupling reaction with unactivated brominated alkanes affording a series of trisubstituted olefins. This tandem reaction exhibits mild conditions, a broad substrate scope, high regioselectivity, and excellent Z/E stereoselectivity. A series of controlled experiments have shown that the critical 1,4‐Ni migration process is reversible. In addition, the alkenyl nickel intermediates obtained after migration are highly Z/E stereoselective and do not undergo Z/E isomerization. The obtained trace isomerization products are caused by the instability of the product.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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