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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.

SUBMITTER: Wallach DR

PROVIDER: S-EPMC5010445 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

Wallach Daniel R DR Chisholm John D JD

The Journal of organic chemistry 20160810 17

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 th ...[more]

PMID: 27487402

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