Highly Selective Coupling of Alkenes and Aldehydes Catalyzed by [Ni(NHC){P(OPh)3}]: Synergy between a Strong σ Donor and a Strong π Acceptor
- 12 January 2007
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 46 (5) , 782-785
- https://doi.org/10.1002/anie.200603907
Abstract
Give and take: Both a strong electron donor (1) and a strong electron acceptor (P(OPh)3) are necessary for a highly selective, nickel‐catalyzed coupling reaction between alkenes, aldehydes, and silyl triflates (see scheme; cod=cycloocta‐1,5‐diene, Tf=trifluoromethanesulfonyl). This synergistic effect may also be useful in other transformations catalyzed by NHC–metal complexes (NHC=N‐heterocyclic carbene).Keywords
This publication has 41 references indexed in Scilit:
- Nickel-Catalyzed Coupling of Alkenes, Aldehydes, and Silyl TriflatesJournal of the American Chemical Society, 2006
- The Value of a NickelScience, 2005
- An N‐Heterocyclic Carbene/Iridium Hydride Complex from the Oxidative Addition of a Ferrocenyl–Bisimidazolium Salt: Implications for SynthesisAngewandte Chemie, 2004
- Comparing Nickel- and Palladium-Catalyzed Heck ReactionsOrganometallics, 2004
- Oxidative Addition of Imidazolium Salts to Ni0 and Pd0: Synthesis and Structural Characterization of Unusually Stable Metal–Hydride ComplexesAngewandte Chemie International Edition in English, 2004
- Oxidative Addition of Imidazolium Salts to Ni0 and Pd0: Synthesis and Structural Characterization of Unusually Stable Metal–Hydride ComplexesAngewandte Chemie, 2004
- Quantitative analysis of ligand effects. Part 3. Separation of phosphorus(III) ligands into pure .sigma.-donors and .sigma.-donor/.pi.-acceptors. Comparison of basicity and .sigma.-donicityOrganometallics, 1989
- Phosphine-induced reductive elimination from cis-arylmethylnickel(II) complexes having a 1,2-bis(dimethylphosphino)ethane ligandOrganometallics, 1983
- Lewis-acid catalyzed ene reactionsAccounts of Chemical Research, 1980
- Organo (dipyridyl) nickel complexes. I. Stability and activation of the alkyl-nickel bonds of dialkyl (dipyridyl) nickel by coordination with various substituted olefinsJournal of the American Chemical Society, 1971