H2O as the Hydrogen Donor: Stereo-Selective Synthesis of E- and Z-Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes

H2O 作为氢供体:通过钯催化炔烃半氢化立体选择性合成 E- 和 Z- 烯烃

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作者:Jianwu Shi, Taowen Ye, Jin Dong, Aifen Liu, Tong Xu, Mingliang Tai, Lei Zhang, Chengniu Wang

Abstract

It is very desirable to develop a facile controllable method for selective semihydrogenation of alkynes to alkenes with a cheap and safe hydrogen donor but remains a big challenge. H2O is one of the best choices of the transfer hydrogenation agent of the world, and the development of methods for synthesizing E- and Z-alkenes using H2O as the hydrogen source is worthwhile. In this article, a palladium-catalyzed synthesis of E- and Z-alkenes from alkynes using H2O as the hydrogenation agent was reported. The use of di-tert-butylphosphinous chloride (t-Bu2PCl) and triethanolamine/sodium acetate (TEOA/NaOAc) was essential for the stereo-selective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 48 alkenes, with good yields and high stereoselectivities.

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