Synfacts 2008(4): 0359-0359  
DOI: 10.1055/s-2008-1042850
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Three-Component Synthesis of 2,3,5-Triaryl Pyridines

Contributor(s): Victor Snieckus, Johnathan Board
J. Barluenga*, A. Jiménez-Aquino, M. A. Fernández, F. Aznar, C. Valdés
Universidad de Oviedo, Spain
Further Information

Publication History

Publication Date:
19 March 2008 (online)


A palladium-catalyzed, three-component synthesis of 2,3,5-triaryl-substituted pyr­idines is reported. The reaction system was devised incrementally and hence a good understanding of the individual steps has resulted. The first step, Pd-catalyzed coupling of alkenylbromide with morpholine, yields an activated alkene. Palladium catalysis also induces the coupling of the alkenylbromide with the silylimine to form the 2-aza-1,3-buta­diene. Lewis acid catalysis with Yb(OTf)3 then facilitates a Diels-Alder reaction which, after elimination of morpholine and oxidation, yields the ­pyridine derivative.