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Preparation of Palladium(II) Complexes of 1-substituted-3-phospholene Ligands and their Evaluation as Catalysts in Hydroalkoxycarbonylation

[ Vol. 23 , Issue. 25 ]

Author(s):

Péter Bagi*, Réka Herbay, Gábor Györke, Péter Pongrácz, László Kollár, István Timári, László Drahos and György Keglevich   Pages 2873 - 2879 ( 7 )

Abstract:


A series of palladium(II) complexes incorporating 1-substituted-3-methyl-3- phospholenes as the P-ligands were prepared from phospholene oxides by deoxygenation followed by complexation with PdCl2(PhCN)2. The two 1-substituted-3-methyl-3- phospholene ligands were trans position to each other in the Pd(II)-complexes. As the ligands contain a P-stereogenic center, the Pd-complexes were obtained as a 1:1 mixture of two stereoisomers, the homochiral (R,R and S,S) and the meso (R,S) forms, when racemic starting materials were used. An optically active Pd-complex containing (R)-1-propyl- 3-phospholene ligand was also prepared. Catalytic activity of an aryl- and an alkyl-3- phospholene-palladium(II)-complex was evaluated in hydroalkoxycarbonylation of styrene. The alkyl-derivative showed higher activity and selectivity towards the formation of the esters of 3-phenylpropionic acid. However, the overall activity of these PdCl2(phospholene)2-type complexes was low.

Keywords:

3-Phospholene oxides, deoxygenation, 3-phospholenes, palladium complexes, hydroalkoxycarbonylation.

Affiliation:

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111 Budapest, Department of Inorganic Chemistry, University of Pécs and János Szentágothai Science Center, MTA-PTE Research Group for Selective Chemical Syntheses, H-7624 Pécs, Department of Inorganic Chemistry, University of Pécs and János Szentágothai Science Center, MTA-PTE Research Group for Selective Chemical Syntheses, H-7624 Pécs, Department of Inorganic and Analytical Chemistry, University of Debrecen, H- 4032 Debrecen, MS Proteomics Research Group, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1117, Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111 Budapest

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