Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies

被引：143

作者：

Shekhar, K. C. ^{[1
]}

Dhungana, Roshan K. ^{[1
]}

Shrestha, Bijay ^{[1
]}

Thapa, Surendra ^{[1
]}

Khanal, Namrata ^{[1
]}

Basnet, Prakash ^{[1
]}

Lebrun, Robert W. ^{[1
]}

Giri, Ramesh ^{[1
]}

机构：

[1] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 31期

基金：

美国国家科学基金会;

关键词：

CROSS-COUPLING REACTIONS; ALKENYL CARBONYL-COMPOUNDS; ARYL GRIGNARD-REAGENTS; ALKYL-HALIDES; UNACTIVATED OLEFINS; INTERMOLECULAR CYANOTRIFLUOROMETHYLATION; TRANSIENT METALLACYCLES; ASYMMETRIC-SYNTHESIS; TERMINAL ALKENES; HECK REACTIONS;

D O I：

10.1021/jacs.8b05374

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a Ni-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arylzinc reagents to generate 1,1-diarylalkanes. The reaction proceeds well with primary, secondary and tertiary alkyl halides, and electronically diverse arylzinc reagents. Mechanistic investigations by radical probes, competition studies and quantitative kinetics reveal that the current reaction proceeds via a Ni(0)/Ni(I)/Ni(II) catalytic cycle by a rate-limiting direct halogen atom abstraction via single electron transfer to alkyl halides by a Ni(0)-catalyst.

引用

页码：9801 / 9805

页数：5

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