Efficient Photodecarboxylation of Trifluoromethyl-substituted Phenylacetic and Mandelic Acids

Authors


Corresponding author email: mlukeman@acadiau.ca (Matthew Lukeman)

Abstract

A total of eight CF3-substituted phenylacetic and mandelic acids are shown to undergo efficient photodecarboxylation (PDC; Φ = 0.37–0.74) in basic aqueous solution to give the corresponding trifluoromethyltoluenes or trifluoromethylbenzyl alcohols. The products are consistent with the almost exclusive formation of benzylic carbanions that subsequently react with water, with minor amounts (≤5%) of radical-derived products detected. Quenching studies indicate that the reaction likely proceeds from the singlet excited state. This work demonstrates that the CF3 group greatly facilitates the excited state ionic PDC of phenylacetic acids.

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