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用于异腈与乙烯基芳烃的 Mizoroki-Heck 交叉偶联的光催化异腈 C(sp)-N 键活化

Photocatalyzed C(sp)-N Bond Activation of Isonitriles for Mizoroki-Heck Cross-Coupling with Vinyl Arenes.

作者信息

Wood Allanah B, Mizuno Natsuki, Jung Sarah, Schuppe Alexander W

机构信息

Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.

出版信息

Org Lett. 2025 Sep 5;27(35):9716-9720. doi: 10.1021/acs.orglett.5c02954. Epub 2025 Aug 26.

Abstract

We report a Mizoroki-Heck reaction enabled by the visible-light-induced Pd-catalyzed C-N bond cleavage of isonitriles. Through a one-carbon activation of amines, we eliminated the need for atom-inefficient activating groups, thereby allowing isonitriles to serve as alkyl radical precursors. The utility of this protocol was demonstrated with a variety of (hetero)aromatic-containing isonitriles and differentially substituted vinyl arenes. This transformation expands the range of cross-coupling reactions that amine precursors can undergo.

摘要

我们报道了一种可见光诱导的钯催化异腈C-N键裂解实现的 Mizoroki-Heck 反应。通过胺的单碳活化,我们消除了对原子效率低下的活化基团的需求,从而使异腈能够作为烷基自由基前体。该方法的实用性通过多种含(杂)芳基的异腈和不同取代的乙烯基芳烃得到了证明。这种转化扩展了胺前体可以进行的交叉偶联反应的范围。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/51db/12418498/0dab59f5e951/ol5c02954_0001.jpg

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