Radical Sulfimidation via Visible-Light Photoredox Catalysis: N -Acyloxyamides as Bench-Stable Nitrene Surrogates

Herein, we describe a visible-light-driven sulfimidation of thioethers with N-acyloxyamides catalyzed by TPT. The protocol proceeds under ambient conditions, tolerates a broad range of functional groups, and delivers the desired products in yields of up to 99%. The gram-scale reaction retains full efficiency with 1 mol % catalyst loading. Products such as N-allyl-N-(thio)amides, N-sulfonyl sulfimides, and N-acyl sulfoximines could be readily afforded with the methodology. Preliminary mechanistic investigations suggest that a radical cross-coupling pathway might be involved.