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J Org Chem. 2004 Feb 20;69(4):1221-6.

Pd(OAc)2-catalyzed oxidative coupling reaction of benzenes with olefins in the presence of molybdovanadophosphoric acid under atmospheric dioxygen and air.

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  • 1Department of Applied Chemistry, Faculty of Engineering, Kansai University, Suita, Osaka 564-8680, Japan.

Abstract

The direct oxidative coupling reaction of benzenes with alkenes bearing an electron-withdrawing group was successfully achieved by the use of Pd(OAc)(2)/molybdovanadophosphoric acid (HPMoV) as the key catalyst under O(2) or air atmosphere. Thus, the reaction of benzene with ethyl acrylate under air (1 atm) assisted by Pd(OAc)(2)/HPMoV afforded ethyl cinnamate as a major product in satisfactory yield (74%). This catalytic system could be extended to the coupling reactions between various substituted benzenes and alkenes through the direct aromatic C-H bond activation. In the reaction of benzene with ethyl acrylate under O(2) (1 atm), the best turn-over number (TON) of Pd(OAc)(2) reached was 121. This reaction provides a green route to cinnamate derivatives, which are important precursors of a variety of pharmaceuticals.

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