Synthesis 2007(4): 529-540  
DOI: 10.1055/s-2007-965896
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Intramolecular Arylation of N-Benzyl-2-iodoimidazoles: A Facile and Rapid Access to 5H-Imidazo[2,1-a]isoindoles

Renata Marcia de Figueiredo, Sylviane Thoret, Caroline Huet, Joëlle Dubois*
Institut de Chimie des Substances Naturelles-CNRS, avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: joelle.dubois@icsn.cnrs-gif.fr;
Further Information

Publication History

Received 15 September 2006
Publication Date:
18 January 2007 (online)

Abstract

The first example of a Pd-catalyzed intramolecular aryl­ation involving the C-2 position of an imidazole ring is presented. Application of this reaction led to the formation of 5H-imidazo[2,1-a]isoindole in one step from N-benzyl-2-iodoimidazole. Microwave irradiation enhanced the rate of reaction allowing the synthesis of various imidazo[2,1-a]isoindole analogues.