6533b836fe1ef96bd12a1470

RESEARCH PRODUCT

Catalytic Efficiency of a New Tridentate Ferrocenyl Phosphine Auxiliary: Sonogashira Cross-Coupling Reactions of Alkynes with Aryl Bromides and Chlorides at Low Catalyst Loadings of 10-1 to 10-4 mol %.

Maurice SantelliVladimir V. IvanovJean-cyrille HiersoHenri DoucetRégine AmardeilPhilippe MeunierAziz Fihri

subject

DenticityArylOrganic ChemistrySonogashira couplingHalideGeneral MedicineBiochemistryCoupling reactionCatalysischemistry.chemical_compoundchemistryPolymer chemistryOrganic chemistryPhysical and Theoretical ChemistryCatalytic efficiencyPhosphine

description

[structure: see text] The catalytic activity in Sonogashira cross-coupling reactions of alkynes with a variety of aryl halides (including chlorides) using a multidentate ferrocenyl phosphine is presented. The novel mixed ferrocenyl aryl/alkyl triphosphine is thermally stable and insensitive to air or moisture, and its robustness allows aryl alkynylation at 10(-1) to 10(-4) mol % catalyst loadings with TONs up to 250,000. Copper-free coupling using phenylacetylene is also accessible in good yield.

https://doi.org/10.1002/chin.200502088