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Electrochemical Azidoarylthiation of Aryl Olefin and Enol Ethers
Rongxin Yang1, Fuqiao Xing1, Hongjian Song1
1State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, People's Republic of China.
Abstract:
We have developed a green electrochemical method for azidoarylthiation of styrenes and enol ethers by employing trimethylsilyl azide as a nucleophile and diaryl disulfides and aryl thiols as atom-economical arylthio sources under oxidant- and metal-free conditions. β-Azido aryl sulfides were obtained in moderate to good yields, and the reaction showed good functional group tolerance. This method avoids the formation of 1,2-disulfides and 1,2-diazides and controls the regioselectivity of the reactions while providing a good starting point for the synthesis of functionalized β-amino aryl sulfides and triazolo aryl sulfides.
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