Synthesis and application of ortho-palladated complex of (4-phenylbenzoylmethylene)triphenylphosphorane as a highly active catalyst in the Suzuki cross-coupling reaction

The ortho-metallated complex [Pd(μ-Cl){κ2(C,C)-[C6H4(PPh2CHC(O)C6H4-Ph-4)}]2 (2a) was prepared by refluxing of Pd(OAc)2 and {(Ph)3PCHCOC6H4-Ph-4} (PhBPPY) of in CH2Cl2 followed by addition of an excess of KCl in MeOH Complex (2a) reacts with triphenylphosphine to give the mononuclear derivative [Pd(Cl)(PhC6H4COCHPPh2C6H4)(PPh3)] (3a) whose crystal structure has been determined by single crystal X-ray diffraction. The Suzuki reactions of aryl bromides and chlorides of varying electron density using complex (3a) as an efficient catalyst were performed, giving the cross-coupling products in good to excellent yields.

A new ortho-palladated complex of phosphorus ylide was tested as catalyst in the Suzuki–Miyaura cross-coupling reactions of aryl bromides and chlorides. Figure optionsDownload as PowerPoint slideResearch highlights
► The ortho-palladated complex [Pd(Cl)(PhC6H4COCHPPh2C6H4)(PPh3)] (3a) was prepared by refluxing of Pd(OAc)2 and {(Ph)3PCHCOC6H4-Ph-4} (PhBPPY) of in CH2Cl2 followed by addition of an excess of KCl in MeOH, then triphenylphosphine was added to suspension and to give the mononuclear derivative (3a).
► The crystal structure of ortho-palladated complex [Pd(Cl)(PhC6H4COCHPPh2C6H4)(PPh3)] (3a) has been determined by single crystal X-ray diffraction.
► The ortho-palladated complex (3a) as an efficient catalyst was used in the Suzuki cross-coupling reaction and giving the cross-coupling products in good to excellent yields.
► Suzuki cross-coupling reactions carried out under air atmosphere and optimized conditions; in the experiments we used similar conditions (solvent, base, mol% of catalyst and completion reaction time).