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Article Dans Une Revue Green Chemistry Année : 2018

A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate

Liang Chang
Nadja Klipfel
  • Fonction : Auteur
Luc Dechoux
  • Fonction : Auteur
Serge Thorimbert

Résumé

A novel, efficient, and environmentally compatible method for CF3-substituted benzene production is reported. It sources a bio-based feedstock, employs tBuOK as catalyst, and is solvent-free. This regioselective approach provides various trifluoromethyl benzenes in good to excellent yields, without extra oxidant or special care. CO2 and water are the only byproducts of this process, and reaction conditions can scale up to gram quantities. The transformation involves an unprecedented tBuOK-catalyzed domino process, and features Michael addition / 6π-electrocyclic ring opening / [1,5]-H shift / carba-6π-electrocyclic ring closure / decarboxylative aromatization reactions.

Domaines

Chimie organique
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Dates et versions

hal-01720637 , version 1 (01-03-2018)

Identifiants

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Liang Chang, Nadja Klipfel, Luc Dechoux, Serge Thorimbert. A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate. Green Chemistry, 2018, 20, pp.1491-1498. ⟨10.1039/C7GC03721J⟩. ⟨hal-01720637⟩
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