Visible Light-Induced Synthesis of Sulfenamides via Oxidative Coupling of Amines with Thiols
Yifan Li, Wenjing Yang, Shuicai Chen, Cong‐Ying Zhou, Zhen Guo
Abstract
Herein, we report a visible light-induced synthesis of sulfenamides via the oxidative coupling of amines with thiols using O 2 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 O 2 under visible light irradiation. This radical intermediate couples to form disulfide, which subsequently undergoes aminolysis to produce sulfenamides.
Topics & Concepts
ChemistryOxidative phosphorylationCoupling (piping)Oxidative coupling of methaneCombinatorial chemistryPhotochemistryVisible spectrumOrganic chemistryBiochemistryCatalysisOptoelectronicsMechanical engineeringEngineeringPhysicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCaching and Content Delivery