Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of O-Arylhydroxylamines and Substituted Benzofurans
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Buchwald_Pd-Catalyzed O.pdf
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Author(s)
Maimone, Thomas
Buchwald, Stephen Leffler
Date Issued
July 2010
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Maimone, Thomas J., and Stephen L. Buchwald. “Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of O-Arylhydroxylamines and Substituted Benzofurans.” Journal of the American Chemical Society 132.29 (2010): 9990–9991.
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Author's final manuscript
Abstract
An efficient Pd catalyst for the O-arylation of ethyl acetohydroximate with aryl chlorides, bromides, and iodides has been developed. Ethyl acetohydroximate serves as an efficient hydroxylamine equivalent for C−O cross-coupling, thereby allowing for the preparation of O-arylhydroxylamines from simple aryl halides. Short reaction times and broad substrate scope, including heteroaryl coupling partners, allow access to O-arylhydroxylamines that would be difficult to prepare in a single step by traditional methods. Moreover, the O-arylated products so formed can be directly transformed into substituted benzofurans in a single operation.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja1044874
