title: Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.
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.
authors.affiliation: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Wallach
authors.affiliation: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University , Syracuse, New York 13244, United States.
authors.forename: John D
authors.initials: JD
authors.lastname: Chisholm
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000478:Alkylation; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D062845:Chloroacetates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D066244:Proton Magnetic Resonance Spectroscopy; D013449:Sulfonamides / Q000737:chemistry*; D013696:Temperature
chemical_list: D000081:Acetamides; D062845:Chloroacetates; D013449:Sulfonamides; C009528:trichloroacetamide