Review of recent advances in CF bond activation of aliphatic fluorides

• This review covers compounds with a CF bond, CF2 or CF3.
• Various organic compounds are synthesized through CF bond activation.
• Aliphatic fluorides could be activated by Lewis acid, Brønsted superacids or hydrogen bonding.
• The cleavage of CF bond could be mediated by transition-metal or rare earth metal.
• Dehydrofluorination by a base or SN2′ displacement by a nucleophile could be a method for leaving of a fluoride.

CF bond activation of aliphatic fluorides provides new methodologies for synthesis of new fluorinated building blocks as well as versatile non-fluorinated products. This review covers the recent CF bond cleavage examples and further transformation of compounds bearing with an aliphatic fluoride, difluoromethylene group or trifluoromethyl groups. The methods to activate a CF bond include activation by Lewis acid, Brønsted superacids and hydrogen bonding, and mediation by transition-metals and rare earth metals. Partial reduction of trifluoromethyl group through a single electron transfer (SET) process can provide the compounds with less fluorine. Bases are often used for the elimination of hydrofluoride. SN2′ displacement is also an important method for transformation of monofluorinated, difluorinated and trifluorinated olefins to various synthetically interesting molecules.

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