Oxford University Press (OUP) Acta Medica Okayama 0366-7022 53 11 2024 SNAr hexafluoroisopropoxylation of electron-rich aryl fluoride with a catalytic electrical input upae196 EN Eisuke Sato Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Tomohiro Nakahama Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Koichi Mitsudo Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Seiji Suga Division of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University Anodic oxidation–promoted SNAr reactions of electron-rich aryl fluoride were developed. The anodic oxidation of 4-fluoroanisole in hexafluoroisopropyl alcohol (HFIP) with K2CO3 led to SNAr-type hexafluoroisopropoxylation, and the reaction was completed with a catalytic electrical input. The results of cyclic voltammetry suggest that the radical cation of 4-fluoroanisole, which would react with the alkoxide of HFIP, is generated. Electron transfer between the intermediate and the starting material constructs the catalytic cycle, and the elimination of fluoride from the Meisenheimer complex produces the desired compound. No potential conflict of interest relevant to this article was reported.