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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

 and *
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)
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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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Mieczyńska, E.; Trzeciak, A.M. Selective Heck Arylation of Cyclohexene with Homogeneous and Heterogeneous Palladium Catalysts. Molecules 2010, 15, 2166-2177.

AMA Style

Mieczyńska E, Trzeciak AM. Selective Heck Arylation of Cyclohexene with Homogeneous and Heterogeneous Palladium Catalysts. Molecules. 2010; 15(4):2166-2177.

Chicago/Turabian Style

Mieczyńska, Ewa; Trzeciak, Anna M. 2010. "Selective Heck Arylation of Cyclohexene with Homogeneous and Heterogeneous Palladium Catalysts." Molecules 15, no. 4: 2166-2177.


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