Organic Letters
Organic Letters
5 years ago

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

Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide
Bin Shuai, Xiu-Jie Zhang, Yue-Gang Chen, Cong Ma, Ping Fang, Tian-Sheng Mei
An efficient Ni-catalyzed reductive carboxylation of allylic alcohols with CO2 has been successfully developed, providing 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 hydrogenation to give allylic alcohol intermediates, followed by carboxylation. A preliminary mechanistic investigation suggests that the hydrogenation step is made possible by a Ni hydride intermediate produced by a hydrogen atom transfer from water.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01208

DOI: 10.1021/acs.orglett.7b01208

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