Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide

Yue-Gang Chen , Bin Shuai , Cong Ma, Xiu-Jie Zhang, Ping Fang and Tian-Sheng Mei*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China, Email: mei7900sioc.ac.cn

Y.-G. Chen, B. Shuai, C. Ma, X.-J. Zhang, P. Fang, T.-S. Mei, Org. Lett., 2017, 19, 2969-2972.

DOI: 10.1021/acs.orglett.7b01208

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Abstract

An efficient Ni-catalyzed reductive carboxylation of brached and linear allylic alcohols with CO₂ provides linear β,γ-unsaturated carboxylic acids as the sole regioisomer with generally high E/Z stereoselectivity. In addition, the carboxylic acids can be generated from propargylic alcohols via a hydrogenation step made possible by a Ni hydride intermediate produced by a hydrogen atom transfer from water.

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Key Words

carboxylation, allylation, manganese

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ID: J54-Y2017