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

Chao Liu, Xiaoqing Wang, Zhaodong Li, Lei Cui and Chaozhong Li*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China, Email: cligmail.sioc.ac.cn

C. Liu, X. Wang, Z. Li, L. Cui, C. Li, J. Am. Chem. Soc., 2015, 137, 9820-9823.

DOI: 10.1021/jacs.5b06821

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Abstract

With AgNO₃ as the catalyst and K₂S₂O₈ as the oxidant, an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids with tosyl azide or pyridine-3-sulfonyl azide in aqueous MeCN 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.

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Key Words

alkyl azides, potassium peroxydisulfate

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ID: J48-Y2015