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Synfacts 2005(2): 0210-0210  
DOI: 10.1055/s-2005-916068
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Heteroaromatic Amines by C-N Cross-Coupling

Contributor(s): V. Snieckus, Oleg M. Demchuk
M. D. Charles, P. Schultz, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

C-N cross-coupling of heteroaromatic halides with a variety of aromatic, heteroaromatic, and aliphatic amines catalyzed by bulky, electron-rich phosphino-palladium complexes is reported. Coupling of a wide range of heteraromatic halides, even with unprotected NH functionalities, proceeds in good to excellent yields. Activated and unactivated heteroaryl chlorides and bromides may be used; examples include 5-bromopyrimidine, substituted thiophenes, benzoxazoles and benzothiazoles as well as 5- and 6-haloindoles.