Electrochemical Azidoarylthiation of Aryl Olefin and Enol Ethers

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.