Iodine Promoted Regioselective alpha-Sulfenylation of Carbonyl Compounds using Dimethyl Sulfoxide as an Oxidant

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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Abstract

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
Publication:	ORGANIC LETTERS
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
URI:	http://eprints.iisc.ac.in/id/eprint/55910

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