Sonogashira Coupling Using Bulky Palladium-Phenanthryl Imidazolium Carbene Catalysis

Abstract

[structure: see text] Bulky phenanthracenyl imidazolium-derived carbene ligands were investigated for copper-free Sonogashira coupling with terminal acetylenes. Aryl bromides and iodides gave coupled products in excellent yields from the Pd(PPh(3))(2)Cl(2) complex with potassium t-butoxide and 18-crown-6 in THF. A remarkable dependence on the size of the ligand was found. The highest yields were obtained with the bulky 2,9-dicyclohexyl-10-phenanthryl ligand 5.