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Molecules 2010, 15(4), 2166-2177; doi:10.3390/molecules15042166

Selective Heck Arylation of Cyclohexene with Homogeneous and Heterogeneous Palladium Catalysts

Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, Poland
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Received: 27 January 2010 / Revised: 10 March 2010 / Accepted: 23 March 2010 / Published: 25 March 2010
(This article belongs to the Special Issue Heck Coupling)
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Abstract

Palladium catalysts containing Pd(II) supported on Al2O3 and alumina-based mixed oxides, Al2O3-ZrO2, Al2O3-CeO2, and Al2O3-Fe2O3, are very effective in the Heck coupling of iodobenzene with cyclohexene in DMF solution. The best results, up to 81% of monoarylated products with a selectivity to 4-phenylcyclohexene (3) close to 90% were obtained with KOH as a base. The catalytic activity of palladium supported on alumina-based oxides was compared with that of homogeneous precursors, such as Pd(OAc)2 and PdCl2(PhCN)2, used in [Bu4N]Br as the reaction medium. Under such conditions homogeneous systems were more selective and produced up to 60% of monoarylated products with a selectivity to 3 close to 60%.
Keywords: palladium; Heck coupling; heterogenized catalysts; cyclohexene palladium; Heck coupling; heterogenized catalysts; cyclohexene
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Mieczyńska, E.; Trzeciak, A.M. Selective Heck Arylation of Cyclohexene with Homogeneous and Heterogeneous Palladium Catalysts. Molecules 2010, 15, 2166-2177.

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