Synthesis of Substituted Oxindoles from α-Chloroacetanilides via Palladium-Catalyzed C−H Functionalization
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- 13 September 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (40), 12084-12085
- https://doi.org/10.1021/ja037546g
Abstract
A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed.Keywords
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