ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

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.

[img] PDF
Org_Let_18-23_6090_2016.pdf - Published Version
Restricted to Registered users only

Download (1066Kb) | Request a copy
Official URL: http://dx.doi.org/10.1021/acs.orglett.6b03084

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
Related URLs:
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.ernet.in/id/eprint/55910

Actions (login required)

View Item View Item