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A simple, modular synthesis of substituted pyridines.

ABSTRACT: A simple, modular method to prepare highly substituted pyridines is disclosed. The method employs a cascade reaction comprising (1) a novel N-iminative, Cu-catalyzed cross-coupling of alkenylboronic acids at the N-O bond of alpha,beta-unsaturated ketoxime O-pentafluorobenzoates, (2) electrocyclization of the resulting 3-azatriene, and (3) air oxidation affording highly substituted pyridines in moderate to excellent isolated yields (43-91%). Starting materials are readily available, and functional group tolerance is very good.

SUBMITTER: Liu S

PROVIDER: S-EPMC2664531 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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A simple, modular synthesis of substituted pyridines.

Liu Songbai S Liebeskind Lanny S LS

Journal of the American Chemical Society 20080509 22

A simple, modular method to prepare highly substituted pyridines is disclosed. The method employs a cascade reaction comprising (1) a novel N-iminative, Cu-catalyzed cross-coupling of alkenylboronic acids at the N-O bond of alpha,beta-unsaturated ketoxime O-pentafluorobenzoates, (2) electrocyclization of the resulting 3-azatriene, and (3) air oxidation affording highly substituted pyridines in moderate to excellent isolated yields (43-91%). Starting materials are readily available, and functiona ...[more]

PMID: 18465855

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