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Updated: Jun 2, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Silver-catalyzed C-C bond formation between methane and ethyl diazoacetate in supercritical CO₂
Ana Caballero1, Emmanuelle Despagnet-Ayoub, M Mar Díaz-Requejo
1Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al Consejo Superior de Investigaciones Científicas, Centro de Investigación en Química Sostenible, Universidad de Huelva, Campus de El Carmen, 21007-Huelva, Spain.
Abstract:
Even in the context of hydrocarbons' general resistance to selective functionalization, methane's volatility and strong bonds pose a particular challenge. We report here that silver complexes bearing perfluorinated indazolylborate ligands catalyze the reaction of methane (CH(4)) with ethyl diazoacetate (N(2)CHCO(2)Et) to yield ethyl propionate (CH(3)CH(2)CO(2)Et). The use of supercritical carbon dioxide (scCO(2)) as the solvent is key to the reaction's success. Although the catalyst is only sparingly soluble in CH(4)/CO(2) mixtures, optimized conditions presently result in a 19% yield of ethyl propionate (based on starting quantity of the diazoester) at 40°C over 14 hours.
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Catalysis

