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Intramolecular Fe(II)-Catalyzed N-O or N-N Bond Formation from Aryl Azides

Benjamin J. Stokes, Carl V. Vogel, Linda K. Urnezis, Minjie Pan and Tom G. Driver*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois, 60607-7061, Email: tgduic.edu

B. J. Stokes, C. V. Vogel, L. K. Urnezis, M. Pan, T. G. Driver, Org. Lett., 2010, 12, 2884-2887.

DOI: 10.1021/ol101040p (free Supporting Information)


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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 various functional groups and facilitates access to a range of benzisoxazoles or indazoles.

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Key Words

benzo-fused N-heterocycles, benzo-fused O-heterocycles


ID: J54-Y2010-1760