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Published on: August 1, 2018
Visible Light-Induced Synthesis of Sulfenamides via Oxidative Coupling of Amines with Thiols
Yifan Li1, Wenjing Yang1, Shuicai Chen2
1College of Materials Science & Engineering, Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, Taiyuan University of Technology, Taiyuan, Shanxi 030024, People's Republic of China.
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.
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