title: Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (hetero)aryl bromides: efficient and complementary approach to 3-acyl-2-oxindoles.
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.
authors.affiliation: Center for Insoluble Protein Structures (inSPIN), Interdisciplinary Nanoscience Center (iNANO), and Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C (Denmark).
authors.forename: Zhong
authors.initials: Z
authors.lastname: Lian
authors.forename: Stig D
authors.initials: SD
authors.lastname: Friis
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D001965:Bromides / Q000737:chemistry*; D002247:Carbon Isotopes; D002248:Carbon Monoxide; D002384:Catalysis; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis; D015195:Drug Design; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*
chemical_list: D001965:Bromides; D002247:Carbon Isotopes; D016861:Cyclooxygenase Inhibitors; D006571:Heterocyclic Compounds; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D010165:Palladium; D002248:Carbon Monoxide; C062866:tenidap
keywords: carbonylation; isotope labeling; oxindoles; palladium; α-arylation