Kumada–Tamao–Corriu Coupling of Alkyl Halides Catalyzed by an Iron–Bisphosphine Complex
- 5 September 2011
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 40 (9), 1030-1032
- https://doi.org/10.1246/cl.2011.1030
Abstract
An iron(II) chloride complex possessing a sterically demanding ortho-phenylene-tethered bisphosphine ligand shows a high catalytic activity in the Kumada–Tamao–Corriu coupling of nonactivated alkyl halides with aryl Grignard reagents. Primary, secondary, and tertiary alkyl halides can participate as an electrophilic coupling partner. A radical clock experiment using (iodomethyl)cyclopropane exclusively gives the corresponding ring-opening coupling product, suggesting intermediacy of alkyl radical species.Keywords
This publication has 37 references indexed in Scilit:
- Low-Valent Iron-Catalyzed C−C Bond Formation−Addition, Substitution, and C−H Bond ActivationThe Journal of Organic Chemistry, 2010
- Coming of Age: Sustainable Iron‐Catalyzed Cross‐Coupling ReactionsChemSusChem, 2009
- The Promise and Challenge of Iron-Catalyzed Cross CouplingAccounts of Chemical Research, 2008
- Iron-catalysed carbon–heteroatom and heteroatom–heteroatom bond forming processesChemical Society Reviews, 2008
- Advances in Iron Catalyzed Cross Coupling ReactionsChemistry Letters, 2005
- Iron-Catalyzed Reactions in Organic SynthesisChemical Reviews, 2004
- Transition Metal‐Catalyzed Carbon−Carbon Bond Formation with Grignard Reagents − Novel Reactions with a Classic ReagentEuropean Journal of Organic Chemistry, 2004
- Iron catalyzed cross-coupling reactions. Synthesis of arylethenes.Tetrahedron Letters, 1983
- Couplage mixte entre sulfones vinyliques et réactifs de grignard en présence de sels de métal de transition: synthèse stéréosélective d'oléfines trisubstituées.Tetrahedron Letters, 1982
- Vinylation of Grignard reagents. Catalysis by ironJournal of the American Chemical Society, 1971