Use of a bulky phosphine of weak σ-donicity with palladium as a versatile and highly-active catalytic system: Allylation and arylation coupling reactions at 10-1-10-4 mol% catalyst loadings of ferrocenyl bis(difurylphosphine)/Pd

Carbon-carbon(sp2-sp2 and sp1-sp 2) and carbon-nitrogen (nucleophilic allylation) coupling processes are promoted by a catalytic system containing [PdCl(η3-C 3H5)]2 with the new ferrocenyl bis(difurylphosphine) 1,1′-bis[di(5-methyl-2-furyl)phosphino]ferrocene, Fc[P(FuMe)2]2. Starting from aryl bromides or allylic acetates this versatile catalyst system may be used at low palladium loadings (10-1-10-4 mol%) in some Heck, Suzuki, Sonogashira and allylic amination reactions to give cross-coupled products in excellent yield. Remarkably high activity is obtained in allylic substitution reactions, providing a significant impetus for the development of bulky phosphines possessing weak σ-donicity for this particular reaction. © 2005 Elsevier Ltd. All rights reserved.