Synfacts 2009(7): 0785-0785  
DOI: 10.1055/s-0029-1217264
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium(II)-Catalyzed Olefination of Electron-Deficient Arenes

Contributor(s): Paul Knochel, Tobias Thaler
Y.-H. Zhang, B.-F. Shi, J.-Q. Yu*
The Scripps Research Institute, La Jolla, USA
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22. Juni 2009 (online)


A meta-selective palladium(II)-catalyzed olefination of highly electron-deficient arenes is described. Hereby, the 2,6-dialkylpyridine ligands which display minimal steric hindrance at the immediate surrounding of the nitrogen atom but bear bulky groups on the carbon-side chains play a crucial role. The method is very general and shows a high tolerance towards functional groups. The reaction proceeds regioselectively with a preference for the meta-olefinated product.