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EtAlCl2/2,6-Disubstituted Pyridine-Mediated Carboxylation of Alkenes with Carbon Dioxide
Shinya Tanaka1, Kota Watanabe1, Yuuki Tanaka1
1Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University , 6-6-11 Aramaki-Aoba, Aoba-ku, Sendai 980-8579, Japan.
Abstract:
α-Arylalkenes and trialkyl-substituted alkenes undergo carboxylation with CO2 in the presence of EtAlCl2 and 2,6-dibromopyridine to afford the corresponding α,β- and/or β,γ-unsaturated carboxylic acids. This reaction is suggested to proceed via the electrophilic substitution of EtAlCl2 with the aid of the base, followed by the carbonation of the resulting ate complex. This reaction can be applied to terminal dialkylalkenes by using a mixture of 2,6-di-tert-butylpyridine and 2,6-dibromopyridine.
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