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Synthesis 2009(3): 369-371  
DOI: 10.1055/s-0028-1083314
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Desulfurization of Thioamides into Amides with H2O2/ZrCl4 Reagent System

Kiumars Bahrami*a,b, Mohammad Mehdi Khodaei*a,b, Yeganeh Tirandaza
a Department of Chemistry, Razi University, Kermanshah 67149, Iran
b Nanoscience and Nanotechnology Research Center (NNRC), Razi University, Kermanshah 67149, Iran
Fax: +98(831)4274559; e-Mail: kbahrami2@hotmail.com; e-Mail: mmkhoda@razi.ac.ir;
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Publication History

Received 22 August 2008
Publication Date:
09 January 2009 (online)

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Abstract

The hydrogen peroxide/zirconium(IV) chloride reagent system has been used as a new and efficient reagent for the deprotection/desulfurization of thioamides to amides. This system is reasonably general and can be applied to the conversion of several thioamides to the corresponding amides. The salient features of this protocol are short reaction times, good chemoselectivity, cleaner reaction profiles, and simple workup that precludes the use of toxic solvents.

Key words

deprotection - thioamides - amides - desulfurization - hydrogen peroxide