A scalable and operationally simple radical trifluoromethylation

Joel W. Beatty, James J. Douglas, Kevin P. Cole and Corey R. J. Stephenson ()
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Joel W. Beatty: University of Michigan
James J. Douglas: University of Michigan
Kevin P. Cole: Small Molecule Design and Development, Lilly Research Laboratories, Eli Lilly and Company
Corey R. J. Stephenson: University of Michigan

Nature Communications, 2015, vol. 6, issue 1, 1-6

Abstract: Abstract The large number of reagents that have been developed for the synthesis of trifluoromethylated compounds is a testament to the importance of the CF3 group as well as the associated synthetic challenge. Current state-of-the-art reagents for appending the CF3 functionality directly are highly effective; however, their use on preparative scale has minimal precedent because they require multistep synthesis for their preparation, and/or are prohibitively expensive for large-scale application. For a scalable trifluoromethylation methodology, trifluoroacetic acid and its anhydride represent an attractive solution in terms of cost and availability; however, because of the exceedingly high oxidation potential of trifluoroacetate, previous endeavours to use this material as a CF3 source have required the use of highly forcing conditions. Here we report a strategy for the use of trifluoroacetic anhydride for a scalable and operationally simple trifluoromethylation reaction using pyridine N-oxide and photoredox catalysis to affect a facile decarboxylation to the CF3 radical.

Date: 2015
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms8919

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DOI: 10.1038/ncomms8919

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