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

Article

Selective Heck Arylation of Cyclohexene with Homogeneous and Heterogeneous Palladium Catalysts

Ewa Mieczyńska and Anna M. Trzeciak*

Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, Poland

* Author to whom correspondence should be addressed.

Received: 27 January 2010; in revised form: 10 March 2010 / Accepted: 23 March 2010 / Published: 25 March 2010

(This article belongs to the Special Issue Heck Coupling)

Download PDF Full-Text [415 KB, uploaded 25 March 2010 15:16 CET]

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

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