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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Iron-Catalyzed Oxidative C-H/C-H Cross-Coupling between Electron-Rich Arenes and Alkenes
Yiyang Ma1, Dongchao Zhang1, Zhiyuan Yan1
1†College of Chemistry and Molecular Sciences, the Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, People's Republic of China.
Abstract:
A novel oxidative C-H/C-H cross-coupling reaction between electron-rich arenes and alkenes is established utilizing FeCl3 as the catalyst and DDQ as the oxidant. Interestingly, direct arylation products are obtained with diaryl-ethylenes and double arylation products are obtained with styrene derivatives, which show high chemoselectivity and good substrate scope. A radical trapping experiment and EPR (electron paramagnetic resonance) experiments indicate that this reaction proceeds through a radical pathway in which DDQ plays a key role in the aryl radical formation. XAFS (X-ray absorption fine structure) experiments reveal that the oxidation state of the iron catalyst does not change during the reaction, suggesting that FeCl3 might be used as a Lewis acid. Finally, a detailed mechanism is proposed for this transformation.
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