Palladium-Catalyzed Carbonylative alpha-Arylation of 2-Oxindoles with (Hetero)aryl Bromides: Efficient and Complementary Approach to 3-Acyl-2-oxindoles

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An efficient Pd-catalyzed carbonylative alpha-arylation of 2-oxindoles with aryl and heteroaryl bromides for the one-step synthesis of 3-acyl-2-oxindoles has been developed. This reaction proceeds efficiently under mild conditions and is complementary to the more common oxindole forming reactions. The transformation only requires a mild base and provides good to excellent yields even with heteroaromatic substrates. Employing a near stoichiometric amount of (13)COgen, the methodology was easily extended to [C-13] acyl labeling. The general applicability of the reaction conditions was demonstrated in the synthesis of a structure related to the pharmaceutically active 3-acyl-2-oxindoles, tenidap.
Original languageEnglish
JournalAngewandte Chemie International Edition
Volume53
Issue36
Pages (from-to)9582-9586
Number of pages5
ISSN1433-7851
DOIs
Publication statusPublished - 1 Sep 2014

    Research areas

  • alpha-arylation, carbonylation, isotope labeling, oxindoles, palladium, C BOND FORMATION, SILACARBOXYLIC ACIDS, H FUNCTIONALIZATION, COUPLING REACTIONS, SITU GENERATION, CARBON-MONOXIDE, OXINDOLES, 1,3-DIKETONES, DERIVATIVES, TENIDAP

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