Biocatalytic trifluoromethylation of unprotected phenols

Robert C. Simon (), Eduardo Busto, Nina Richter, Verena Resch, Kendall N. Houk () and Wolfgang Kroutil ()
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Robert C. Simon: Organic and Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz
Eduardo Busto: Organic and Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz
Nina Richter: ACIB GmbH
Verena Resch: Organic and Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz
Kendall N. Houk: University of California
Wolfgang Kroutil: Organic and Bioorganic Chemistry, University of Graz, NAWI Graz, BioTechMed Graz

Nature Communications, 2016, vol. 7, issue 1, 1-6

Abstract: Abstract Organofluorine compounds have become important building blocks for a broad range of advanced materials, polymers, agrochemicals, and increasingly for pharmaceuticals. Despite tremendous progress within the area of fluorination chemistry, methods for the direct introduction of fluoroalkyl-groups into organic molecules without prefunctionalization are still highly desired. Here we present a concept for the introduction of the trifluoromethyl group into unprotected phenols by employing a biocatalyst (laccase), tBuOOH, and either the Langlois’ reagent or Baran’s zinc sulfinate. The method relies on the recombination of two radical species, namely, the phenol radical cation generated directly by the laccase and the CF3-radical. Various functional groups such as ketone, ester, aldehyde, ether and nitrile are tolerated. This laccase-catalysed trifluoromethylation proceeds under mild conditions and allows accessing trifluoromethyl-substituted phenols that were not available by classical methods.

Date: 2016
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DOI: 10.1038/ncomms13323

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