Hydroxycarbonylation of styrene with palladium catalysts: The influence of the mono- and bidentate phosphorus ligand

• Published in: Journal of molecular catalysis. A, Chemical Vol. 161; no. 1; pp. 39 - 48
• Main Authors: del Rı́o, Inmaculada, Ruiz, Nuria, Claver, Carmen, van der Veen, Lars A., van Leeuwen, Piet W.N.M.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 06.11.2000; Elsevier
• Subjects: Carbonylation; Catalysis; Catalytic reactions; Chemistry; Exact sciences and technology; General and physical chemistry; Palladium; Phosphine ligand; Regioselectivity; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Phosphine ligand; Carbonylation; Palladium; Catalysis; Regioselectivity; Ligand effect; Catalytic reaction; Hydrocarbon; Palladium Complexes; Phosphine; Transition metal Complexes; Phosphorus Compounds; Precursor; Bidentate ligand; Styrene; Reaction mechanism; Benzenic compound; Platinoid Complexes; Catalyst; Ethylenic compound
• ISSN: 1381-1169; 1873-314X
• DOI: 10.1016/S1381-1169(00)00359-9

A systematic study of the hydroxycarbonylation reaction of styrene is described. The effect of the catalytic precursor and the reaction conditions on the results of the reaction was investigated. Several monophosphines (PPh 3, P(p-Tol) 3, P(p-C 6H 4OMe) 3, P(p-C 6H 4F) 3, PPh 2(o-Tol), PMe 3, PCy 3) and diphosphines (dppe, dppp, dppb, dppf, HomoXantphos, DPEphos, Xantphos, BDPP, BINAP, BPPFA, DIOP) were applied to control the regioselectivity of the reaction. The effect of the bite angle of the diphosphines has also been studied. Catalysts containing monophosphines as ligands give 2-phenylpropanoic acid as the major product and the 3-phenyl propanoic acid is obtained when diphosphines are used. Two catalytic cycles are proposed to explain the influence of the different palladium precursors with mono- and diphosphines.