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Synthesis of Substituted Oxindoles from α-Chloroacetanilides via Palladium-Catalyzed C-H Functionalization

Edward J. Hennessy and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

E. J. Hennessy, S. L. Buchwald, J. Am. Chem. Soc., 2003, 125, 12084-12085.

DOI: 10.1021/ja037546g (free Supporting Information)


Abstract

A highly regioselective palladium-catalyzed cyclization converts α-chloroacetanilides to oxindoles in good to excellent yields with high functional group compatibility using 2-(di-tert-butylphosphino)biphenyl as ligand and triethylamine as a stoichiometric base.

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Key Words

Oxindoles, Lactams


ID: J48-Y2003-1610