Beneficial effect of carboxylic acid additives on the Pd-catalyzed intramolecular N-arylation of 2-amino-3-(2-chlorophenylsulfonyl)pyrroles

Perounsack X. Moon, Chad E. Stephens

    Research output: Contribution to journalArticlepeer-review

    4 Scopus citations

    Abstract

    Carboxylic acid additives have been shown to significantly improve the yield of the Pd-catalyzed intramolecular N-arylation of 2-aminopyrroles containing a 2-chlorophenylsulfonyl group at the 3-position to give a novel tricyclic ring system. Pivalic and phenylacetic acid provided the best yield enhancement, while acetic acid showed moderate enhancement. Other acids showed limited to no enhancement or even a detrimental effect on the reaction.

    Original languageEnglish (US)
    Pages (from-to)6226-6229
    Number of pages4
    JournalTetrahedron Letters
    Volume54
    Issue number46
    DOIs
    StatePublished - Nov 13 2013

    Keywords

    • 2-Aminopyrrole
    • Buchwald-Hartwig reaction
    • Carboxylic acid additive
    • Intramolecular
    • N-arylation
    • Pyrrolo[3,2-b]benzo[1,4]thiazine

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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