Ortho-SelectiveCross-Coupling of Fluorobenzenes with Grignard Reagents: Accelerationby Electron-Donating Ortho-DirectingGroups

Fluorobenzenes with directing groups such as hydroxy, hydroxymethyl, and ammo underwent ortho-selective cross-coupling with Grignard reagents in the presence of palladium-based catalysts, with dichlorobis(tricyclohexylphosphine)palladium [PdCl 2 (PCy 3 ) 2 ] found to be the optimum catalyst. Fluoro and chloro groups at positions other than ortho to the directing groups survived under the reaction conditions.