氟烷基化策略的最新进展:探索砜基和亚砜基试剂在单、双和三氟甲基化反应中的新型活性和合成应用

Synthesis Pub Date : 2024-09-05 DOI:10.1055/s-0043-1775391
Alexander Knieb, G. K. Surya Prakash
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引用次数: 0

摘要

氟烷基化是化学家精确改变小分子性质的关键策略。在已有的氟烷基化方案中,砜试剂和亚砜试剂是这些反应的多功能工具,特别是在单氟、双氟和三氟甲基化反应中。它们的多功能性在于提供了多种途径,包括亲电、亲核以及自由基机制,从而通过各种非常令人兴奋的机理途径,为受控分子修饰提供了多样化的途径。1 引言 2 单氟甲基化策略 2.1 氟双(苯磺酰)甲烷(FBSM) 2.2 2-氟-1,3-苯并二硫醚-1,1,3,3-四氧化物(FBDT) 2.3 苯并噻唑-SO2CH2F、NaSO2CH2F 和 ClSO2CH2F 2.4 PhSO2CH2F 3 二氟甲基化策略 3.1 PhSO2CF2H 3.2 苯并噻唑-SO2CF2H 3.3 2-PyrSO2CF2H 3.4 NaSO2CF2H 4 三氟甲基化策略 4.1 PhSO2CF3 4.2-PyrSO2CF3 4.3 苯并噻唑-SO2CF3 4.4 NaSO2CF3 4.4.1 电化学方法 4.4.2 光化学方法 4.4.3 其他值得注意的方法 5 结论
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Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations

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

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