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Issue 7, 2018
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A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate

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Abstract

A novel, efficient, and environmentally compatible method for CF3-substituted benzene production is reported. It sources a bio-based feedstock, employs tBuOK as a catalyst, and is solvent-free. This regioselective approach provides various trifluoromethyl benzenes in good to excellent yields, without any extra oxidant or special care. CO2 and water are the only byproducts of this process, and the 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.

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

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Supplementary files

Article information


Submitted
11 Dec 2017
Accepted
12 Feb 2018
First published
13 Feb 2018

Green Chem., 2018,20, 1491-1498
Article type
Paper

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, 20, 1491
DOI: 10.1039/C7GC03721J

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