337488-10-5Relevant academic research and scientific papers
Iodine Promoted Regioselective α-Sulfenylation of Carbonyl Compounds using Dimethyl Sulfoxide as an Oxidant
Siddaraju, Yogesh,Prabhu, Kandikere Ramaiah
, p. 6090 - 6093 (2016)
A metal-free regioselective sulfenylation of the α-CH3 group of ketones has been achieved in the presence of the α-CH2 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 I2 and DMSO. The application of this methodology has been demonstrated by synthesizing precursors for Julia- Kocienski olefination intermediates.
