A metal-free regioselective sulfenylation of the α-CH group of ketones has been achieved in the presence of the α-CH or α-CH group using the cross dehydrogenative (CDC) strategy. Aldehydes also exhibit good selectivity forming the corresponding α-sulfenylated products. This efficient sulfenylation of ketones or aldehydes with thiones or heterocyclic thiols utilizes dimethyl sulfoxide (DMSO) as an oxidant in the presence of iodine. This eco-friendly method uses readily available and inexpensive I and DMSO. The application of this methodology has been demonstrated by synthesizing precursors for Julia- Kocienski olefination intermediates.
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