ja5b06821_si_001.pdf (2.66 MB)
Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution
journal contribution
posted on 2015-08-12, 00:00 authored by Chao Liu, Xiaoqing Wang, Zhaodong Li, Lei Cui, Chaozhong LiWe
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.