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Mild and Highly Chemoselective Oxidation of Thioethers Mediated by Sc(OTf)3

Mizio Matteucci, Gurdip Bhalay and Mark Bradley*

*University of Edinburgh, School of Chemistry, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom, Email: mark.bradleyed.ac.uk

M. Matteucci, G. Bhalay, M. Bradley, Org. Lett., 2003, 5, 235-237.

DOI: 10.1021/ol026947i (free Supporting Information)


Abstract

Sc(OTf)3 is an efficient catalyst for the hydrogen peroxide mediated monooxidation of alkyl-aryl sulfides and methyl cysteine containing peptides. The method is high yielding, compatible with many widely used protecting groups, suitable for solid-phase applications and proceeds with minimum over-oxidation.

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Key Words

Oxidation, Sulfoxides, Hydrogen peroxide


ID: J54-Y2003-290