It Takes Alkynes to Make a World - New Methods for Dehydrobenzoannulene Synthesis

Michael M. Haley

doi:10.1055/s-1998-5736

Synlett 1998; 1998(6): 557-565
DOI: 10.1055/s-1998-5736

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It Takes Alkynes to Make a World - New Methods for Dehydrobenzoannulene Synthesis

Michael M. Haley^*

^*Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA; Fax 5 41-3 46-04 87; E-mail: haley@oregon.uoregon.edu

Abstract

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Recent advances in the assembly of dehydrobenzoannulenes (DBAs) are the subject of this account. Using in situ generated acetylenic intermediates, novel α,ω-polyynes can be easily constructed using Pd-catalyzed alkynylation methodology. Subsequent cyclization via intra- and intermolecular Cu-mediated reactions can provide a wide variety of DBAs, including heretofore inaccessible topologies, systems with an unprecedented number of acetylenic linkages, structures with derivatized aromatic rings, and unusual organometallic species.

alkynes - annulenes - carbon allotropes - copper-mediated dimerizations - palladium cross-coupling reactions

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