Iodophor-catalyzed sulfenylation of indoles with sulfonyl hydrazides for the synthesis of 3-sulfenylindoles

Abstract

An iodophor-catalyzed sulfenylation of indoles using sulfonyl hydrazides as sulfur source to synthesize 3-sulfenylindoles in aqueous phase has been achieved. Notably, iodophor as catalyst and solvent is inexpensive, commercially available and no innocuous to the environment. The method is also easy to operate. Moreover, the synthetic strategy features a wide range of substrates with excellent tolerance to diverse functional groups. A plausible mechanism for the iodophor-mediated 3-sulfenylation of indoles with sulfonyl hydrazides has been proposed. In addition, 3-(phenylthio)-1H-indole was obtained on a multi-gram scale.