BODIPY Photocatalyzed Beckmann Rearrangement and Hydrolysis of Oximes under Visible Light

J Org Chem. 2022 Sep 16;87(18):11958-11967. doi: 10.1021/acs.joc.2c00813. Epub 2022 Aug 31.

Abstract

A novel, efficient, and mild protocol for rearrangement of oximes to amides or hydrolyzing to ketone/aldehyde using a simple BODIPY dye as a photocatalyst and air as an oxidant via propagation reaction under visible-light irradiation is reported. The triplet excited state of BODIPY played a significant role in the catalytic process. It was found that the various substituted ketoximes, both with electron-withdrawing and electron-donating substituents, afforded the corresponding products with moderate to excellent yields, and the catalytic efficiency was up to 0.01 mol %.