Synthesis 2004(15): 2527-2534  
DOI: 10.1055/s-2004-831205
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Synthetic Strategy of N-Arylated Heterocycles via Sequential Palladium-Catalyzed Intra- and Inter-Arylamination Reactions

Rafik Omar-Amrani, Raphaël Schneider*, Yves Fort*
Synthèse Organométallique et Réactivité, UMR CNRS-UHP 7565, Faculté des Sciences, BP 239, 54506 Vandoeuvre les Nancy Cedex, France
Fax: +33(3)83684785; e-Mail: Raphael.Schneider@sor.uhp-nancy.fr; Yves.Fort@sor.uhp-nancy.fr;
Further Information

Publication History

Received 19 May 2004
Publication Date:
02 September 2004 (online)

Abstract

The use of an in situ generated Pd(0) catalyst associated to N,N′-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as a ligand and t-BuONa as the base for sequential intra- followed by intermolecular aryl amination is described. The method has been applied to the synthesis of N-arylated five-, six- and seven-membered nitrogen heterocycles.

15

SIPr·HCl is commercially available from Strem Chemicals Inc.