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Intramolecular Fe(II)-catalyzed N-O or N-N bond formation from aryl azides.

ABSTRACT: Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.

SUBMITTER: Stokes BJ

PROVIDER: S-EPMC2913475 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Intramolecular Fe(II)-catalyzed N-O or N-N bond formation from aryl azides.

Stokes Benjamin J BJ Vogel Carl V CV Urnezis Linda K LK Pan Minjie M Driver Tom G TG

Organic letters 20100601 12

Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated plan ...[more]

PMID: 20507088

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