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Convenient One-Pot Synthesis of Sulfonamides and Sulfonyl Azides from Thiols Using N-Chlorosuccinimide

Hojat Veisi*, Ramin Ghorbani-Vaghei, Saba Hemmati, Jafar Mahmoodi

*Department of Chemistry, Payame Noor University, 19395-4697 Tehran, I. R. of Iran, Email: hojatveisiyahoo.com

H. Veisi, R. Ghorbani-Vaghei, S. Hemmati, J. Mahmoodi, Synlett, 2011, 2315-2320.

DOI: 10.1055/s-0030-1261232 (free Supporting Information)


Abstract

In situ preparation of sulfonyl chlorides from thiols by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water followed by reaction with amine or sodium azide in the same reaction vessel enables a convenient synthesis of sulfonamides and sulfonyl azides.

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Key Words

N-chlorosuccinimide, sulfonyl chlorides, sulfonamides, sulfonyl azides


ID: J60-Y2011-2810