Photocatalytic Strategy for Decyanative Transformations Enabled by Amine-Ligated Boryl Radical.

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: January 2025

Decyanation after α-functionalization by exploiting the inherent properties of cyano groups enables the strategic assembly of a carbon scaffold. Herein, we demonstrate an amine-ligated boryl radical-mediated cyano group transfer (CGT) strategy of malononitriles under photocatalytic conditions. This strategy allows for the cleavage of C(sp)-CN and the formation of C(sp)-D and C(sp) to realize decyanative deuteration and cyclization via radical-polar crossover. Computational studies successfully demonstrated the reactivity of CGT promoters can be accurately assessed.

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http://dx.doi.org/10.1021/acs.orglett.4c04701DOI Listing

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