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Molecules 2011, 16(2), 1804-1824; doi:10.3390/molecules16021804

New Chiral P-N Ligands for the Regio- and Stereoselective Pd-Catalyzed Dimerization of Styrene

1 Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, Via Licio Giorgieri 1, 34127 Trieste, Italy 2 Department de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C. Marcel.lí Domingo s/n 43007 Tarragona, Spain
* Author to whom correspondence should be addressed.
Received: 27 December 2010 / Revised: 17 February 2011 / Accepted: 18 February 2011 / Published: 22 February 2011
(This article belongs to the Special Issue Homogeneous Catalysis)
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Two new chiral, enantiomerically pure, hybrid P-N ligands, namely (2R,5S)-2-phenyl-3-(2-pyridyl)-1,3-diaza-2-phosphanicyclo[3,3,0]octan-4-one (1) and (2R,5S)-2-phenyl-3-(2-pyridyl)-1,3-diaza-2-phosphanicyclo[3,3,0]octane (2), have been synthesized starting from L-proline. The two ligands differ in the presence or not of a carbonyl group in the diazaphosphane ring. Their coordination chemistry towards Pd(II) was studied by reacting them with [Pd(CH3)Cl(cod)]. A different behaviour was observed: ligand 2 shows the expected bidentate chelating behaviour leading to the mononuclear Pd-complex, while ligand 1 acts as a terdentate ligand giving a dinuclear species. The corresponding cationic derivatives were obtained from the palladium neutral complexes, both as mono- and dinuclear derivatives, and tested as precatalysts for styrene dimerization, yielding E-1,3-diphenyl-1-butene regio- and stereoselectively as the sole product. A detailed analysis of the catalytic behaviour is reported.
Keywords: hybrid phosphorus-nitrogen ligands; palladium; alkene dimerization hybrid phosphorus-nitrogen ligands; palladium; alkene dimerization
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Fanfoni, L.; Meduri, A.; Zangrando, E.; Castillon, S.; Felluga, F.; Milani, B. New Chiral P-N Ligands for the Regio- and Stereoselective Pd-Catalyzed Dimerization of Styrene. Molecules 2011, 16, 1804-1824.

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