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

The Journal of Organic Chemistry
Hanyang BaoYunkui Liu

Abstract

We herein describe a B2Pin2-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4- d2 in a high deuteration ratio by using readily available ethanol- d1 as the deuterium source.

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Citations

Oct 23, 2019·Chemical Communications : Chem Comm·Trinadh KaicharlaJohannes F Teichert
Mar 11, 2021·The Journal of Organic Chemistry·Menghui SongXi-Cun Wang
Mar 9, 2021·Journal of Pharmaceutical and Biomedical Analysis·Armen ShamirianScott S Mitchell
Jun 22, 2021·Chemical Communications : Chem Comm·Byoung Yong ParkMin Su Han
Nov 11, 2020·Organic Letters·Samantha E SloaneJoseph R Clark

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