Ring-opening fluorination via C–C bond cleavage: An efficient approach to diverse fluorinated molecules

Abstract

The unique and desirable properties of fluorinated compounds in pharmaceutical, agrochemical, and materials sciences have driven the development of remote fluorination methods. In particular, the C–C cleavage/fluorination of cyclic molecules recently emerged as one of the most reliable approaches, allowing the efficient construction of otherwise inaccessible fluorinated molecules. While serving as a powerful platform, many ring-opening fluorination methods have relied on the use of expensive and/or low atom-economical electrophilic fluorine sources and often require precious metals such as silver or iridium, impeding their general applications in synthesis and 18F radioisotope studies. In this Perspective, we summarize the recent efforts on the C–C deconstructive fluorination methods, including our new approaches to synthesize remotely-fluorinated ketones, followed by future opportunities of this field toward better sustainability and positron emission tomography (PET) compatibility using earth-abundant element catalysts and simple nucleophilic fluoride salts as fluorine sources.

Keywords

• Fluorination
• C-C bond activation
• Earth abundant elements
• Catalysis
• Radical