One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal–Knorr synthesis of pyrrole derivatives catalyzed by TCCA

Abstract

A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu₄NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.

Keywords:

• thiols
• disulfides
• sulfonic esters
• pyrroles
• TCCA

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Corrigendum

Acknowledgement

We are thankful to Department of Chemistry, Islamic Azad University-Saveh Branch and Payame Noor University (PNU) for partial support of this work.

Notes

This article was originally published with errors. This version has been corrected. Please see corrigendum (http://dx.doi.org/10.1080/17415993.2012.757440).