Electrochemical 1,3-Alkyloxylimidation of Arylcyclopropane Radical Cations: Four-Component Access to Imide Derivatives

Abstract

Herein, a general electrochemical radical-cation-mediated four-component ring-opening 1,3-alkyloxylimidation of arylcyclopropanes, acetonitrile, carboxylic acids, and alcohols is described, providing a facile and sustainable approach to quickly construct structurally diverse imide derivatives from easily available raw materials in an operationally simple undivided cell. This metal-catalyst-and oxidant-free single-electron oxidation strategy offers a green alternative for the formation of highly reactive cyclopropane-derived radical cations, and this protocol features a broad functional group tolerance.

Electrochemical Formation of Oxazolines by 1,3-Oxyfluorination of Non-activated Cyclopropanes

“…The group of Lei has developed electrochemical oxyfluorination, amino fluorination, and difluorination reactions of arylcyclopropanes using Et 3 N·3HF as a fluorine source . Oxyamination of arylcyclopropanes was established by Zhou et al, using electrochemical oxidation conditions . The same approach was used for oxyhalogenation and oxyalkynylation reactions of arylcyclopropanes by Sheng et al as well as the green synthesis method of β-hydroxy ketones by Huang et al and 1,3-diols by Cai et al A few examples for electrochemical oxidation of cyclopropane integrated into polycyclic systems are known; however, these are limited to the strained compounds with an increased highest occupied molecular orbital (HOMO) level. , Because the high oxidation potential of non-activated cyclopropanes prevents their selective electrochemical activation in the presence of other functional groups, we envisioned electrochemical generation of a reactive species, which would be engaged in the reaction with a C–C bond.…”