TXPhos: a highly stable and efficient ligand designed for ppm level Pd-catalyzed Suzuki–Miyaura coupling in water

Abstract

An easily made and highly efficient terphenylphosphine ligand TXPhos is developed for ppm level Pd-catalyzed Suzuki–Miyaura coupling reactions in aqueous media. The terphenyl skeleton of TXPhos provides high stability and reactivity by increasing steric bulkiness and enhancing Pd–arene interactions, leading to more catalytically active monoligated Pd species. The TXPhos palladacycle is robust to afford excellent product yield under an air atmosphere and highly efficient at shortening the reaction period to minutes under micellar conditions with a TOF up to 40 000 s⁻¹.