Visible Light-Induced Synthesis of Sulfenamides via Oxidative Coupling of Amines with Thiols

Abstract

Herein, we report a visible light-induced synthesis of sulfenamides via the oxidative coupling of amines with thiols using O2 as an oxidant. The photoreaction was conducted under simple and mild conditions, without any photocatalysts, metals, or additives. Detailed mechanistic studies revealed that a sulfur radical is generated through a single-electron transfer from an in situ-generated sulfur anion to O2 under visible light irradiation. This radical intermediate couples to form disulfide, which subsequently undergoes aminolysis to produce sulfenamides.