Multiple vinylation of tribenzotriquinacenes and fenestrindanes at their aromatic peripheries by use of Najera's catalyst

Highly efficient six- and eightfold Heck cross-coupling reactions were carried out with two related convex-concave and saddle-shaped hydrocarbons bearing several ortho-dibromo functionalities at the molecular periphery, viz. the hexabromotribenzotriquinacene 3a and the octabromofenestrindane 4a. In contrast to conventional palladium catalysts, use of Najera's oxime-derived palladacycle catalyst 7 effected exhaustive vinylation with styrene or methyl acrylate in high yield and without concomitant formation of partial cross coupling or reduction products, The hexavinyltribenzotriquinacenes and octavinylfenestrinddnes thus obtained are of interest as potential building blocks for novel organic networks, ((c) Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2005)