6533b7d3fe1ef96bd1261229

RESEARCH PRODUCT

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 10−1–10−4mol% catalyst loadings of ferrocenyl bis(difurylphosphine)/Pd

Aziz FihriPhilippe MeunierHenri DoucetRégine AmardeilJean-cyrille HiersoMaurice Santelli

subject

Substitution reactionAllylic rearrangementChemistryOrganic Chemistrychemistry.chemical_elementSonogashira couplingBiochemistryMedicinal chemistryCoupling reactionCatalysisNucleophileDrug DiscoveryOrganic chemistryAminationPalladium

description

Abstract Carbon–carbon(sp2–sp2 and sp1–sp2) and carbon–nitrogen (nucleophilic allylation) coupling processes are promoted by a catalytic system containing [PdCl(η3–C3H5)]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.

yearjournalcountryeditionlanguage
2005-10-01Tetrahedron
https://doi.org/10.1016/j.tet.2005.06.065