Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH4I as a Redox Catalyst

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• 作者：Yang-ye Jiang ; Qing-Qing Wang ; Sen Liang ; Li-Ming Hu ; R. Daniel Little ; Cheng-Chu Zeng
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：June 3, 2016
• 年：2016
• 卷：81
• 期：11
• 页码：4713-4719
• 全文大小：442K
• 年卷期：0
• ISSN：1520-6904

文摘

An efficient protocol for the synthesis of sulfonamides via the electrochemical oxidative amination of sodium sulfinates has been developed. The chemistry proceeds in a simple undivided cell employing a substoichiometric amount of NH₄I that serves both as a redox catalyst and a supporting electrolyte; in this manner additional conducting salt is not required. A wide range of substrates, including aliphatic or aromatic secondary and primary amines, as well as aqueous ammonia, proved to be compatible with the protocol. Scale-up was possible, thereby demonstrating the practicality of the approach. The electrolytic process avoids the utilization of external oxidants or corrosive molecular iodine and therefore represents an environmentally benign means by which to achieve the transformation.