期刊
ACS CATALYSIS
卷 8, 期 11, 页码 10479-10485出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b03396
关键词
decarboxylation; nickel catalysis; aliphatic acid anhydrides; cross-coupling; alkylation
资金
- Collaborative Innovation Center for Diagnosis and Treatment of Infectious Disease
- Tsing-Peking Centre for Life Science
- 1000 Talents Recruitment Program
We present the anhydride-based decarboxylative alkylation of aryl iodides catalyzed by nickel. This method of decarboxylative coupling works with a broad scope of aliphatic carboxylic anhydrides and tolerates synthetically useful aromatic substituents. Assisted by a redox system of pyridine N-oxide and zinc additives, the current reaction occurs under mild conditions and without the assistance of photocatalyst. Notably, this method features high chemoselectivity toward alkyl migration with mixed aliphatic/aromatic anhydrides. Thus, it provides a powerful synthetic tool to modify high-valued aliphatic carboxylic acids by converting them into mixed anhydrides using readily available aryl carboxylic acids such as p-toluic acid. We propose a catalytic cycle that involves the key steps of free radical-based decarboxylation and subsequent alkyl transfer to nickel that precedes an oxidatively induced C C reductive elimination from Ni(III).
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