Synthesis of cis,cis,cis-1-alkylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentanes

A new strategy to prepare tetradentate or pentadentate diphenylphosphine ligands has been explored from Diels-Alder adducts of fulvenes and maleic anhydride. A tetradentate phosphine ligand, bearing a side chain allowing the formation of a bond with polystyrene resin, has been prepared in seven steps from cyclopentadiene. The cis,cis,cis-1-cyclohexylidene-2,3,4,5-tetrakis(diphenylphosphinomethyl)cyclopentane (Cyclo-Tedicyp) in combination with [PdCl(C3H5)](2) led to an efficient catalyst for the Heck, Suzuki and Sonogashira coupling reactions. (C) 2009 Elsevier Ltd. All rights reserved.