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Palladium‐Catalyzed Carbonylative α‐Arylation of 2‐Oxindoles with (Hetero)aryl Bromides: Efficient and Complementary Approach to 3‐Acyl‐2‐oxindoles
Author(s) -
Lian Zhong,
Friis Stig D.,
Skrydstrup Troels
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404217
Subject(s) - oxindole , chemistry , catalysis , aryl , palladium , combinatorial chemistry , stoichiometry , reaction conditions , base (topology) , carbonylation , organic chemistry , carbon monoxide , mathematics , mathematical analysis , alkyl
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.