Palladium-Catalyzed Direct C-H Olefination of Polyfluoroarenes with Alkenyl Tosylates

The first general examples of palladium-catalyzed direct C-H olefination of polyfluoroarenes using alkenyl tosylates as electrophilic coupling partners are presented. By employing the Pd/L1 catalyst system (L1=N-methyl-2-(2',4'-dimethoxyphenyl)-3-dicyclohexylphosphinoindole), the olefinated polyfluoroarenes can be obtained in good-to-excellent yields. Good structural and functional compatibility are also exhibited. In particular, the steric demanding and heterocyclic alkenyl tosylates react smoothly under this catalyst system. This reaction can be practicably performed on a gram-scale without significantly loss of product yields.