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以异腈作为双功能试剂实现1,6-烯炔的自由基烷基氰化反应

Radical Alkylcyanation of 1,6-Enynes with Isonitriles as Bifunctional Reagents.

作者信息

Huang Zhonghou, Qin Jian, Hu Yuntong, Zhu Shengqing, Chu Lingling

机构信息

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai 201620, China.

出版信息

Org Lett. 2024 Dec 20;26(50):10763-10768. doi: 10.1021/acs.orglett.4c03744. Epub 2024 Dec 9.

Abstract

We report a radical cyano-cyclization of 1,6-enynes with isonitriles via photochemically driven nickel catalysis, forging alkenyl nitrile-tethered γ-lactams under mild conditions. This reaction leverages the photoexcitation of generated nickel (isonitrile) species to facilitate isonitriles serving as alkyl radical precursors and cyanide sources. The reaction accommodates a wide range of substrates, exhibiting excellent regioselectivity and / stereoselectivity.

摘要

我们报道了通过光化学驱动的镍催化实现1,6-烯炔与异腈的自由基氰基环化反应,在温和条件下构建烯基腈连接的γ-内酰胺。该反应利用生成的镍(异腈)物种的光激发,促进异腈作为烷基自由基前体和氰化物源。该反应适用于多种底物,表现出优异的区域选择性和立体选择性。

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