Acid Fluorides in Transition-Metal Catalysis: A Good Balance between Stability and Reactivity

Abstract

Several recent reports outlined the singular reactivity of acid fluorides as excellent electrophiles in transition-metal catalysis. These species undergo oxidative addition of the metal into the C-F bond; then, retention or release of the CO moiety can occur and be controlled by tuning the catalytic system and the reaction parameters. Acid fluorides, which can be derived from carboxylic acids, show good stability and high reactivity in a wide range of possible functionalizations with nucleophiles. Their use provides an interesting alternative to that of the parent carboxylic acid derivatives (acid chlorides, esters, amides, acids, or aldehydes).

Keywords: C−F functionalization; acid fluorides; cross-coupling; decarbonylation; transition-metal catalysis.