Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

Hanyang Bao, Bingwei Zhou, Hongwei Jin*, Yunkui Liu*

*College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People’s Republic of China, Email: jhwei828zjut.edu.cn, ykuiliuzjut.edu.cn

H. Bao, B. Zhou, H. Jin, Y. Liu, J. Org. Chem., 2019, 84, 3579-3589.

DOI: 10.1021/acs.joc.9b00321

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Abstract

A B₂Pin₂-assisted copper-catalyzed semihydrogenation of alkynes provides various alkenes in good to excellent yields with Z-selectivity under mild reaction conditions. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes using readily available ethanol-d₁ as the deuterium source.

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proposed mechanism

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Key Words

semireduction of alkynes, bis(pinacolato)diboron

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ID: J42-Y2019