Iodine/DMSO-catalyzed oxidative deprotection of N-tosylhydrazone for benzoic acid synthesis

Abstract

An oxidative deprotection of tosylhyrdazones has been demonstrated to afford benzoic acids using iodine and DMSO system. This efficient oxidative deprotection protocol offers exceptional functional group toleration under mild reaction conditions without any initiators or bases. Notably, the tosylhydrazone with the heteroaryl ring or with the aryl ring having base-sensitive hydroxyl and ester functional groups smoothly afforded the corresponding benzoic acid analogues under developed conditions. Moreover, this method features short reaction times, high product yields and easy purification by avoiding column-chromatographic purification.