Electrochemical carboxylation of α-fluoroalkyl cyclopropane with CO2 to mono- or difluoropentenoic acid†

Abstract

An electrochemical carboxylation of α-fluoroalkyl cyclopropanes with CO₂ is reported in this work. This approach constitutes a rare example of defluorinative carboxylation of organofluorine compounds with the simultaneous cleavage of C–F and C–C bonds. Accordingly, both α-CF₂H and α-CF₃ cyclopropanes serve as effective substrates, facilitating the synthesis of pentenoic acids with an E-configured monofluoroalkene or gem-difluoroalkene moiety with high chemo- and stereoselectivity. The reaction can be also performed under a nonsacrificial anode system. The synthetic practicality is further highlighted by the diverse functionalizations of the resulting multifunctional fluorinated acids. Cyclic voltammetry studies were performed to provide mechanistic insights into the reaction's origins.