Iodine Promoted Regioselective α-Sulfenylation of Carbonyl Compounds using Dimethyl Sulfoxide as an Oxidant
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.
Siddaraju, Yogesh,Prabhu, Kandikere Ramaiah
supporting information
p. 6090 - 6093
(2016/12/09)
Trends in organocatalytic conjugate addition to enones: an efficient approach to optically active alkynyl, alkenyl, and ketone products
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Paixao, Marcio Weber,Holub, Nicole,Vila, Carlos,Nielsen, Martin,Jorgensen, Karl Anker
supporting information; experimental part
p. 7338 - 7342
(2010/01/06)
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