Photocatalytic Shono-type oxidation of N-alkylamides with hydrogen evolution

Abstract

A C–H alkoxylation reaction of N-alkylamides to N-acyl-N,O-acetals provides a straightforward and versatile method for functionalizing the α-position of amides. This reaction has been conventionally carried out by an electrochemical method (Shono oxidation). Although photoinduced variants are also known, they require sacrificial oxidants and/or the pre-functionalization of the amide substrates. We herein report a photoinduced reaction catalysed by an iridium photosensitizer and nickel bromide that eliminates the need for sacrificial oxidants and the pre-installation of reactive handles on the substrates.