Highly Efficient One-Pot Synthesis of N-Alkyl Sulfonamides from Alcohols Using N-(p-Toluenesulfonyl) Imidazole (Tsim)

Abstract

A facile and efficient method for one-pot synthesis of N-alkyl sulfonamides from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this protocol, treatment of various potassium sulfonylamide salts and alcohols in the presence of TsIm and triethylamine in refluxing DMF furnishes the corresponding N-alkyl sulfonamides in good to excellent yields. This methodology is highly efficient for reaction of various structurally diverse primary and secondary alcohols as well as potassium sulfonylamides. Also, the density functional theoretical calculations are employed to mechanistically study this protocol.

[Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]

GRAPHICAL ABSTRACT

Keywords:

• Alcohol
• N-alkylation
• potassium sulfonylamide salt
• TsIm
• triethylamine (TEA)
• DFT study

Acknowledgments

The authors wish to thank Shiraz University of Technology Research Council for financial support of this work.