Radical–Radical Cross-Coupling for C–S Bond Formation

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• 作者：Zhiliang Huang ; Dongchao Zhang ; Xiaotian Qi ; Zhiyuan Yan ; Mengfan Wang ; Haiming Yan ; Aiwen Lei
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：18
• 期：10
• 页码：2351-2354
• 全文大小：344K
• 年卷期：0
• ISSN：1523-7052

文摘

A new method was demonstrated to overcome the selectivity issue of radical–radical cross-coupling toward the synthesis of asymmetric diaryl thioethers. The preliminary mechanism was revealed by radical-trapping experiments, DFT calculations, and kinetics, etc., indicating that the C–S bond formed through cross-coupling of a thiyl radical and an aryl radical cation. Moreover, the formation of an aryl radical cation instead of the C–H bond cleavage was determined as the rate-limiting step.