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DOI: 10.1055/s-2008-1078521
A Highly Efficient Catalyst for Pd-Catalyzed Amination of Aryl Halides
Contributor(s):Paul Knochel, Tobias ThalerYale University, New Haven and University of Illinois, Urbana, USA
Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure-Activity Relationships
J. Am. Chem. Soc. 2008, 130: 6586-6596
Publication History
Publication Date:
23 July 2008 (online)
Key words
Pd-catalyzed amination - heteroaryl halides - aryl halides - long-lived catalysts
Significance
This article presents an extensive study on the selectivity, scope and structure-activity relations for the Pd-catalyzed amination of (het)aryl halides with primary amines. Aryl iodies, which are known to be more reluctant substrates to Pd-catalyzed amination, were also successfully converted.
Comment
CyPF-t-Bu is shown to be a selective catalyst for monoamination. Its effectiveness is explained by detailed studies on the ligand structure. Thus, the rigidity of the ferrocenyl backbone, the electron-donating character and the steric hindrance of the phosphine groups were identified as essential features of this selective amination catalyst.