Purple light-induced Ritter-type reaction of diazophosphonates: access to α-amido-β-keto phosphonates

Abstract

A Ritter-type reaction of diazophosphonates to synthesize α-amido-β-keto phosphonates has been reported in this study under purple light in the absence of a photocatalyst. This protocol shows that the synthesis of the amide functionality involves in situ generation of a carbene, followed by C–N bond formation with a nitrile. The purple LED irradiation alone is sufficient for the efficient transformation to afford synthetic routes to various amide moieties. A rationalization of the reaction mechanism was well supported by control experiments. A library of α-amido-β-keto phosphonates has been well documented for the synthetic community.