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Pd-catalyzed O-arylation of ethyl acetohydroximate: synthesis of O-arylhydroxylamines and substituted benzofurans.

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.

SUBMITTER: Maimone TJ

PROVIDER: S-EPMC2921654 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Pd-catalyzed O-arylation of ethyl acetohydroximate: synthesis of O-arylhydroxylamines and substituted benzofurans.

Maimone Thomas J TJ Buchwald Stephen L SL

Journal of the American Chemical Society 20100701 29

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 trad ...[more]

PMID: 20604520

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