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Palladium-Catalyzed Decarbonylative Heck Coupling of Aromatic Carboxylic Acids with Terminal Alkenes

Wenqing Yu, Long Liu, Tianzeng Huang, Xiangbing Zhou and Tieqiao Chen*

*Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, China, Email: chentieqiaohnu.edu.cn

W. Yu, L. Liu, T. Huang, X. Zhou, T. Chen, Org. Lett., 2020, 22, 7123-7128.

DOI: 10.1021/acs.orglett.0c02462 (free Supporting Information)


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Abstract

A palladium-catalyzed decarbonylative alkenylation of various benzoic acids with terminal alkenes provides the corresponding internal alkenes in very good yields. The conversion of cinnamic acids and bioactive benzoic acids such as 3-methylflavone-8-carboxylic acid, probenecid, adapalin, and febuxostat demonstrate the synthetic value of this new reaction.

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proposed mechanism



Key Words

Heck Reaction, Unsaturated Amides


ID: J54-Y2020