Photocatalytic Decyanative Radical Addition Based on Cyano Group Transfer Mediated by Amine-Ligated Boryl Radicals.

Org Lett

Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

Published: July 2025


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Article Abstract

Herein, we describe a photocatalytic strategy for decyanative hydrofunctionalization of styrenes with α-heteroatom-substituted acetonitriles. This strategy facilitates the generation of α-heteroatom methyl radicals from acetonitriles through cyano group transfer (CGT) enabled by amine-ligated boryl radicals. The broad applicability of this method is demonstrated by its successful application in late-stage functionalization of bioactive compounds. Combined experimental and computational studies suggest that the strong nucleophilic character of amine-ligated boryl radical is beneficial in facilitating the CGT process.

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http://dx.doi.org/10.1021/acs.orglett.5c02217DOI Listing

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