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 (free Supporting Information)
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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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