Rongalite® mediated highly regioselective aerobic hydroxysulfenylation of styrenes with disulfides: a convenient approach to β-hydroxy sulfides

A highly efficient one-pot synthesis of beta-hydroxy sulfides from styrenes and disulfides under an air atmosphere using inexpensive Rongalite (R) as a promoter at room temperature is reported. The protocol involves hydroxysulfenylation via a radical pathway to afford the addition products in 76-96% yields. The salient features of this methodology include high regioselectivity, utilization of both the organsulfur (R-S-) groups of disulfides, aerial oxidation, operational simplicity, odorless and transition-metal-free conditions. (C) 2015 Elsevier Ltd. All rights reserved.