Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations

This review is dedicated to Prof. H. Ila in honor of her 80^th 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-SO₂CH₂F, NaSO₂CH₂F, and ClSO₂CH₂F

2.4 PhSO₂CH₂F

3 Difluoromethylation Strategies

3.1 PhSO₂CF₂H

3.2 Benzothiazole-SO₂CF₂H

3.3 2-PyrSO₂CF₂H

3.4 NaSO₂CF₂H

4 Trifluoromethylation Strategies

4.1 PhSO₂CF₃

4.2 2-PyrSO₂CF₃

4.3 Benzothiazole-SO₂CF₃

4.4 NaSO₂CF₃

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

Publication History

Received: 11 June 2024

Accepted after revision: 16 July 2024

Article published online:
05 September 2024

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