Photoredox Catalytic Phosphine-Mediated Deoxygenation of Hydroxylamines Enables the Construction of N-Acyliminophosphoranes.

Abstract

The chemistry of phosphoranyl radicals has received increasing attention in recent years. Here, we report the generation of amidyl radicals through photocatalytic deoxygenation of hydroxylamines with triphenylphosphine. This methodology offers a novel and convenient route to a diverse range of N-acyliminophosphoranes in moderate to good yields under visible-light photoredox conditions. Fluorescence quenching experiments suggest that the excited-state of the organic photocatalyst (4CzIPN) was oxidatively quenched by a Cu(II) salt.