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

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

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 alc...

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Veröffentlicht in:Organic letters 2017-06, Vol.19 (11), p.2969-2972
Hauptverfasser: Chen, Yue-Gang, Shuai, Bin, Ma, Cong, Zhang, Xiu-Jie, Fang, Ping, Mei, Tian-Sheng
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container_end_page 2972
container_issue 11
container_start_page 2969
container_title Organic letters
container_volume 19
creator Chen, Yue-Gang
Shuai, Bin
Ma, Cong
Zhang, Xiu-Jie
Fang, Ping
Mei, Tian-Sheng
description 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.
doi_str_mv 10.1021/acs.orglett.7b01208
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title Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide
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