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Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of O-Arylhydroxylamines and Substituted Benzofurans

Thomas J. Maimone and Stephen L. Buchwald*

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

T. J. Maimone, S. L. Buchwald, J. Am. Chem. Soc., 2010, 132, 9990-9991.

DOI: 10.1021/ja1044874 (free Supporting Information)


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Abstract

An efficient Pd catalyst allows the O-arylation of ethyl acetohydroximate as an efficient hydroxylamine equivalent with aryl chlorides, bromides, and iodides. Short reaction times and broad substrate scope allow access to O-arylhydroxylamines that would be difficult to prepare. Moreover, the O-arylated products so formed can be directly transformed into substituted benzofurans in a single operation.

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Key Words

O-Arylation, Hydrolysis, Benzofurans


ID: J48-Y2010-1950