eFluorination of Activated Alcohols Using Collidinium Tetrafluoroborate

Org Lett. 2024 Apr 12;26(14):2697-2701. doi: 10.1021/acs.orglett.3c00976. Epub 2023 May 19.

Abstract

Tertiary C-F bonds are important structural designs; however, they suffer from challenging synthesis. Current methodologies use corrosive amine-HF salts or expensive and hazardous catalysts and reagents. Our group recently introduced collidinium tetrafluoroborate as an efficient fluorinating agent for anodic decarboxyfluorination reactions. Nevertheless, tertiary carboxylic acids are less readily available and more challenging to prepare than their alcohol analogues. Herein we report a practical, mild, and cheap electrochemical method to achieve deoxyfluorination of hindered carbon centers.