Organic Chemistry Portal



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:

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

DOI: 10.1021/jacs.5b06821

see article for more reactions


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.

see article for more examples

Key Words

alkyl azides, potassium peroxydisulfate

ID: J48-Y2015