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European J Org Chem. 2019 Jan 31;2019(4):682-690. doi: 10.1002/ejoc.201801111. Epub 2018 Oct 8.

Cu and Hydroquinone for the Trifluoromethylation of Unprotected Phenols.

Author information

1
Institute of Chemistry NAWI Graz BioTechMed Graz University of Graz Heinrichstraße 28 8010 Graz Austria.
2
Institute of Chemistry NAWI Graz University of Graz Universitätsplatz 1/1 8010 Graz Austria.

Abstract

Fluorination and trifluoromethylation are indispensable tools in the preparation of modern pharmaceuticals and APIs. Herein we present a concept for the introduction of a trifluoromethyl group into unprotected phenols employing catalytic copper(I) iodide and hydroquinone, tBuOOH, and the Langlois' reagent. The method proceeds under mild conditions and exhibits an extended substrate scope compared to the biocatalytic trifluoromethylation using laccase from Agaricus bisporus. Various functional groups such as aldehydes, esters, ethers, ketones and nitriles were tolerated. The hydroquinone-mediated trifluoromethylation reaction allowed accessing trifluoromethylated phenols, which are cumbersome to prepare via previously known chemical methods.

KEYWORDS:

Catalysis; Copper; Hydroquinone; Phenol; Trifluoromethylation

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