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以氢作为氢供体:通过钯催化炔烃的半氢化反应立体选择性合成α-和β-烯烃。

HO as the Hydrogen Donor: Stereo-Selective Synthesis of - and -Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes.

作者信息

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

机构信息

Institute of Interdisciplinary Integrative Medicine Research, Medical School of Nantong University, Nantong 226001, China.

出版信息

ACS Omega. 2023 Mar 17;8(12):11492-11502. doi: 10.1021/acsomega.3c00287. eCollection 2023 Mar 28.

DOI:10.1021/acsomega.3c00287
PMID:37008091
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10061537/
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. HO is one of the best choices of the transfer hydrogenation agent of the world, and the development of methods for synthesizing - and -alkenes using HO as the hydrogen source is worthwhile. In this article, a palladium-catalyzed synthesis of - and -alkenes from alkynes using HO as the hydrogenation agent was reported. The use of di--butylphosphinous chloride (-BuPCl) 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.

摘要

开发一种简便可控的方法,以廉价且安全的氢供体将炔烃选择性半氢化制烯烃是非常可取的,但这仍然是一个巨大的挑战。HO是世界上转移氢化剂的最佳选择之一,开发以HO为氢源合成-和-烯烃的方法是值得的。本文报道了一种钯催化的以HO为氢化剂从炔烃合成-和-烯烃的方法。使用二-丁基氯化膦(-BuPCl)和三乙醇胺/醋酸钠(TEOA/NaOAc)对于炔烃的立体选择性半氢化至关重要。该方法的普遍适用性通过48种以上烯烃的合成得到了突出体现,产率良好且立体选择性高。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/f9350080109e/ao3c00287_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/f813d3bbc834/ao3c00287_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/eb708d58d0ae/ao3c00287_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/8fa68511d65b/ao3c00287_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/5456ef72fa9d/ao3c00287_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/f9350080109e/ao3c00287_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/f813d3bbc834/ao3c00287_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/eb708d58d0ae/ao3c00287_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/8fa68511d65b/ao3c00287_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/5456ef72fa9d/ao3c00287_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fb89/10061537/f9350080109e/ao3c00287_0006.jpg

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