Siddaraju, Yogesh and Prabhu, Kandikere Ramaiah (2016) Iodine Promoted Regioselective alpha-Sulfenylation of Carbonyl Compounds using Dimethyl Sulfoxide as an Oxidant. In: ORGANIC LETTERS, 18 (23). pp. 6090-6093.
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A metal-free regioselective sulfenylation of the alpha-CH3 group of ketones has been achieved in the presence of the alpha-CH2 or alpha-CH group using the cross dehydrogenative (CDC) strategy. Aldehydes also exhibit good selectivity forming the corresponding alpha-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.
|Item Type:||Journal Article|
|Additional Information:||Copy right for this article belongs to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||07 Jan 2017 10:15|
|Last Modified:||07 Jan 2017 10:15|
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