title: Iodine Promoted Regioselective α-Sulfenylation of Carbonyl Compounds using Dimethyl Sulfoxide as an Oxidant.
abstract: A metal-free regioselective sulfenylation of the α-CH3group of ketones has been achieved in the presence of the α-CH2or 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 I2and DMSO. The application of this methodology has been demonstrated by synthesizing precursors for Julia- Kocienski olefination intermediates.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore 560012, Karnataka, India.
authors.forename: Yogesh
authors.initials: Y
authors.lastname: Siddaraju
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science , Bangalore 560012, Karnataka, India.
authors.forename: Kandikere Ramaiah
authors.initials: KR
authors.lastname: Prabhu