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

Abstract

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.