Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions

Daniel R. Wallach, John D Chisholm

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

An intermolecular alkylation of sulfonamides with trichloroacetimidates is reported. This transformation does not require an exogenous acid, base, or transition metal catalyst; instead the addition occurs in refluxing toluene without additives. The sulfonamide alkylation partner appears to be only limited by sterics, with unsubstituted sulfonamides providing better yields than more encumbered N-alkyl sulfonamides. The trichloroacetimidate alkylating agent must be a stable cation precursor for the substitution reaction to proceed under these conditions.

Original languageEnglish (US)
Pages (from-to)8035-8042
Number of pages8
JournalJournal of Organic Chemistry
Volume81
Issue number17
DOIs
StatePublished - Sep 2 2016

ASJC Scopus subject areas

  • Organic Chemistry

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