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

Abstract

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.

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Publication details

The article was received on 11 Dec 2017, accepted on 12 Feb 2018 and first published on 13 Feb 2018


Article type: Paper
DOI: 10.1039/C7GC03721J
Citation: Green Chem., 2018, Accepted Manuscript
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    A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate

    L. CHANG, N. Klipfel, L. Dechoux and S. Thorimbert, Green Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7GC03721J

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