A number of pharmaceutical drugs are trifluoromethylarenes, including the anti-depressant fluoxetine and type 2 diabetes medication sitagliptin phosphate. Direct conversion of aryl C-H bonds to aryl perfluoroalkyl groups would afford a wider variety of drug candidates more quickly than the methods currently used. An iron perfluoroalkyl reagent with a Ag<sup>+</sup> initiator has been shown to convert aryl C-H bonds to perfluoroalkylarenes. The mechanism by which the reaction proceeds is unknown, however. A kinetic isotope effect study shows that C-H bond cleavage is not the rate-limiting step, and a Hammett plot suggests that electrophilic or radical intermediates may be involved. p-bound Fe(arene) compounds were studied as possible intermediates in this reaction.

Investigation of the mechanism of arene perfluoroalkylation by iron perfluoroalkyl reagents

249th National Meeting (2015)

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