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H(2)O as the Hydrogen Donor: Stereo-Selective Synthesis of E- and Z-Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes

[Image: see text] 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. H(2)O is one of the best choices of the transfer hydrogenation agent of the world, and the developmen...

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Detalles Bibliográficos
Autores principales: Shi, Jianwu, Ye, Taowen, Dong, Jin, Liu, Aifen, Xu, Tong, Tai, Mingliang, Zhang, Lei, Wang, Chengniu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10061537/
https://www.ncbi.nlm.nih.gov/pubmed/37008091
http://dx.doi.org/10.1021/acsomega.3c00287
Descripción
Sumario:[Image: see text] 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. H(2)O 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 H(2)O as the hydrogen source is worthwhile. In this article, a palladium-catalyzed synthesis of E- and Z-alkenes from alkynes using H(2)O as the hydrogenation agent was reported. The use of di-tert-butylphosphinous chloride (t-Bu(2)PCl) 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.