Download PDF
Synfacts 2008(8): 0859-0859  
DOI: 10.1055/s-2008-1078521
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

A Highly Efficient Catalyst for Pd-Catalyzed Amination of Aryl Halides

Contributor(s):Paul Knochel, Tobias Thaler
Q. Sheng, T. Ogata, J. F. Hartwig*
Yale 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  
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
23 July 2008 (online)

 PDF Download Permissions and Reprints

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.

   Permissions and Reprints