This review is dedicated to Prof. H. Ila in honor of her 80th birthday
Abstract
Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among the established fluoroalkylation protocols, sulfone and sulfinate reagents stand out as versatile tools for these reactions, particularly in mono-, di-, and trifluoromethylations. Their versatility lies in offering multiple pathways, encompassing electrophilic, nucleophilic, as well as radical mechanisms, thus providing diverse routes for controlled molecular modifications through a variety of very exciting mechanistic paths.
1 Introduction
2 Monofluoromethylation Strategies
2.1 Fluorobis(phenylsulfonyl)methane (FBSM)
2.2 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide (FBDT)
2.3 Benzothiazole-SO2 CH2 F, NaSO2 CH2 F, and ClSO2 CH2 F
2.4 PhSO2 CH2 F
3 Difluoromethylation Strategies
3.1 PhSO2 CF2 H
3.2 Benzothiazole-SO2 CF2 H
3.3 2-PyrSO2 CF2 H
3.4 NaSO2 CF2 H
4 Trifluoromethylation Strategies
4.1 PhSO2 CF3
4.2 2-PyrSO2 CF3
4.3 Benzothiazole-SO2 CF3
4.4 NaSO2 CF3
4.4.1 Electrochemical Approaches
4.4.2 Photochemical Approaches
4.4.3 Other Noteworthy Approaches
5 Conclusion
Key words fluoroalkylation - sulfone - sulfinate - monofluoromethylation - difluoromethylation - trifluoromethylation
