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 %
Authors:
- Jean-Cyrille HiersoJean-Cyrille Hierso
- Aziz FihriAFAziz Fihri
- Régine AmardeilRARégine Amardeil
- Philippe MeunierPMPhilippe Meunier
- Henri DoucetHDHenri Doucet
- Maurice SantelliMSMaurice Santelli
- 27 August 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (20) , 3473-3476
Abstract
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.Keywords
This publication has 26 references indexed in Scilit:
- Efficient Palladium‐Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the ReactionAngewandte Chemie International Edition, 2003
- The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles: Sonogashira Reactions of Unactivated Alkyl Bromides and IodidesJournal of the American Chemical Society, 2003
- Evolution in the Palladium‐Catalyzed Cross‐Coupling of sp‐ and sp2‐Hybridized Carbon AtomsAngewandte Chemie International Edition, 2003
- Homogeneous Catalysts Supported on Soluble Polymers: Biphasic Sonogashira Coupling of Aryl Halides and Acetylenes Using MeOPEG‐Bound Phosphine–Palladium Catalysts for Efficient Catalyst RecyclingChemistry – A European Journal, 2003
- A Versatile Catalyst for the Sonogashira Coupling of Aryl ChloridesAngewandte Chemie International Edition, 2003
- Palladium-Catalyzed Coupling Reactions of Aryl ChloridesAngewandte Chemie International Edition, 2002
- Suzuki−Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt SystemsOrganometallics, 2002
- Oxime Palladacycles: Stable and Efficient Catalysts for Carbon−Carbon Coupling ReactionsOrganic Letters, 2000
- Improved Procedures for the Palladium-Catalyzed Coupling of Terminal Alkynes with Aryl Bromides (Sonogashira Coupling)The Journal of Organic Chemistry, 1998
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995