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Cu-Catalyzed Cascades to Carbocycles: Union of Diaryliodonium Salts with Alkenes or Alkynes Exploiting Remote Carbocations

Fengzhi Zhang, Shoubhik Das, Andrew J. Walkinshaw, Alicia Casitas, Michael Taylor, Marcos G. Suero and Matthew J. Gaunt*

*Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom, Email: mjg32cam.ac.uk

F. Zhang, S. Das, A. J. Wlkinshaw, A. Casitas, M. Taylor, M. G. Suero, M. J. Gaunt, J. Am. Chem. Soc., 2014, 136, 8851-8854.

DOI: 10.1021/ja504361y


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Abstract

Copper-catalyzed cascade reactions between alkenes or alkynes and diaryliodonium salts form carbocyclic products. The reactions proceed via arylation of the unsaturated functional group, formation of a carbocation intermediate that facilitates hydride shift pathways to translocate the positive charge to a remote position, and Friedel-Crafts-type ring formation.

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Key Words

benzocyclohexenes


ID: J48-Y2014