Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution

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• 作者：Chao Liu ; Xiaoqing Wang ; Zhaodong Li ; Lei Cui ; Chaozhong Li
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：August 12, 2015
• 年：2015
• 卷：137
• 期：31
• 页码：9820-9823
• 全文大小：422K
• ISSN：1520-5126

文摘

We report herein an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids. Thus, with AgNO₃ as the catalyst and K₂S₂O₈ as the oxidant, the reactions of various aliphatic carboxylic acids with tosyl azide or pyridine-3-sulfonyl azide in aqueous CH₃CN solution afforded the corresponding alkyl azides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific azidation.