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通过铜/光氧化还原双催化实现末端炔烃的分子间 1,2-双官能化,从而构建三取代烯烃。

Intermolecular 1,2-Difunctionalization of Terminal Alkynes to Access Trisubstituted Alkenes via Copper/Photoredox Dual Catalysis.

机构信息

School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei, Anhui 230009, China.

School of Pharmacy, Anhui University of Chinese Medicine, Hefei, Anhui 230012, China.

出版信息

Org Lett. 2023 Jun 2;25(21):3916-3921. doi: 10.1021/acs.orglett.3c01267. Epub 2023 May 22.

Abstract

We report a copper metallaphotocatalytic 1,2-difunctionalization of terminal alkynes with -hydroxyphthalimide (NHP) esters and readily available silyl reagents (TMSCN and TMSNCS) to access stereodefined trisubstituted alkenes, including ()-alkenyl nitriles and thiocyanates. The reaction proceeds with excellent -stereoselectivity and demonstrates broad compatibility with a wide range of terminal alkynes and NHP esters as alkyl radical precursors. Experimental and computational studies have been performed to gain insight into the reaction mechanism.

摘要

我们报告了铜金属光催化的末端炔烃与 -羟基邻苯二甲酰亚胺(NHP)酯和易得的硅试剂(TMSCN 和 TMSNCS)的 1,2-双官能化反应,以获得立体定义的三取代烯烃,包括()-烯基腈和硫氰酸盐。该反应具有优异的 -立体选择性,并表现出与广泛的末端炔烃和 NHP 酯作为烷基自由基前体的广泛兼容性。进行了实验和计算研究以深入了解反应机制。

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