A facile and sustainable protocol for the thiolation of hydrazones with sodiumsulfinates has been developed in the presence of CuBr2 and DBU in DMF to afford diverse benzylic thioethers. Control experiments reveal a radical pathway involving a thiyl radical as a key intermediate.
sulfonohydrazides has been designed for the efficient construction of benzylic thioethers in excellent yield under mild reaction conditions. The current approach avoids the widely used thiolation reagent, thiols. The commercial availability of the base and reagents, broad substrate scope, and convenient reaction procedure make it an attractive method for benzylic thioether synthesis.