The trifluoromethyl anion (CF3−) is the postulated key intermediate in many fluoroalkylation reactions. Although CF3− was widely believed to be transient in the condensed phase, our recent study showed that this species could be prepared in bulk in solution. Here, we present the unequivocal identification of CF3− by NMR spectroscopy and the reaction chemistry that suggests its intermediacy in nucleophilic trifluoromethylation reactions. We will also discuss the theoretical calculations revealing the nature of CF3− and some recent interest in the X-ray crystallographic characterization of CF3−.

Trifluoromethyl anion (CF3−): What we do and do not know

256th National Meeting (2018)

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