Nickel(0)/Dihydroimidazol-2-ylidene Complex Catalyzed Coupling of Aryl Chlorides and Amines
- 29 March 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (9) , 3029-3036
- https://doi.org/10.1021/jo016352l
Abstract
A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.Keywords
This publication has 47 references indexed in Scilit:
- Unexpected reactivity of two-coordinate palladium–carbene complexes; synthetic and catalytic implicationsChemical Communications, 2001
- A Pd complex of a tridentate pincer CNC bis-carbene ligand as a robust homogenous Heck catalystChemical Communications, 2001
- Catalytic Coupling of Aryl Sulfonates with sp2-Hybridized Nitrogen Nucleophiles: Palladium- and Nickel-catalyzed Synthesis of N-Aryl SulfoximinesSynthesis, 2000
- Aromatic Aminations by Heterogeneous Ni0/C CatalysisAngewandte Chemie International Edition in English, 2000
- Reversible Cleavage of Carbon−Carbon Bonds in Benzonitrile Using Nickel(0)Organometallics, 2000
- Efficient Cross-Coupling of Aryl Chlorides with Aryl Grignard Reagents (Kumada Reaction) Mediated by a Palladium/Imidazolium Chloride SystemJournal of the American Chemical Society, 1999
- General and Efficient Catalytic Amination of Aryl Chlorides Using a Palladium/Bulky Nucleophilic Carbene SystemOrganic Letters, 1999
- Rational Development of Practical Catalysts for Aromatic Carbon−Nitrogen Bond FormationAccounts of Chemical Research, 1998
- Formation of Palladium Bis(amine) Complexes from Reaction of Amine with Palladium Tris(o-tolyl)phosphine Mono(amine) ComplexesOrganometallics, 1996
- Synthesis and Characterization of Polyaniline Derivatives: Poly(2-alkoxyanilines) and Poly(2,5-dialkoxyanilines)Chemistry of Materials, 1995