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\(\hbox {Ph}_{3}\hbox {P/CCl}_{4}\) as a highly efficient reagent for one-pot \(N\)-alkylation of sulfonamides from alcohols: a rapid route to \(N\)-alkyl sulfonamides synthesis

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Abstract

A mild, efficient, and selective protocol for the one-pot \(N\)-alkylation of sulfonamides with alcohols using triphenylphosphine and carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, and potassium sulfonylamide salts in refluxing anhydrous DMF furnishes the corresponding \(N\)-alkyl sulfonamides in good to excellent yields. This protocol is highly efficient for various structurally diverse alcohols and potassium sulfonylamide salts. In this paper the influence of solvents and various reagents as sources for electrophilic-halogen instead of carbon tetrachloride in combination with triphenylphosphine have been examined. This protocol demonstrates the selectivity between primary and secondary alcohols. A plausible mechanism for this protocol has been described.

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Acknowledgments

The authors wish to thank Shiraz University of Technology research council for partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Shiraz University of Technology, Shiraz, 71555-313, Iran

    Mohammad Navid Soltani Rad & Somayeh Behrouz

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  1. Mohammad Navid Soltani Rad
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  2. Somayeh Behrouz
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Correspondence to Mohammad Navid Soltani Rad.

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Rad, M.N.S., Behrouz, S. \(\hbox {Ph}_{3}\hbox {P/CCl}_{4}\) as a highly efficient reagent for one-pot \(N\)-alkylation of sulfonamides from alcohols: a rapid route to \(N\)-alkyl sulfonamides synthesis. Mol Divers 17, 745–752 (2013). https://doi.org/10.1007/s11030-013-9471-9

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