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  • Title: Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (hetero)aryl bromides: efficient and complementary approach to 3-acyl-2-oxindoles.
    Author: Lian Z, Friis SD, Skrydstrup T.
    Journal: Angew Chem Int Ed Engl; 2014 Sep 01; 53(36):9582-6. PubMed ID: 25044569.
    Abstract:
    An efficient Pd-catalyzed carbonylative α-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 [(13) C] 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.
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