Solid-state Silver-catalyzed Ring-opening Fluorination of Cyclobutanols Using Mechanochemistry

In this report, we demonstrate that a ball milling technique facilitates fast and efficient silver-catalyzed ring-opening fluorination of cyclobutanols. This is the first report of a catalytic C–C bond cleavage/functionalization reaction under solid-state mechanochemical conditions. The developed protocol affords a high yield of γ-fluorinated ketones within much shorter reaction times and requires less silver catalyst and Selectfluor® as compared to those under previous solution-based conditions. Notably, the process can be carried out in air. Considering the reduced use of chemicals and the simple, time-saving experimental procedures, this technique is an efficient and environmentally friendly way to access γ-fluorinated ketones.

Publication History

Received: 18 November 2022

Accepted after revision: 29 January 2023

Accepted Manuscript online:
29 January 2023