Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations DOI
G. K. Surya Prakash, Alexander Knieb

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 5, 2024

Abstract Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among established fluoroalkylation protocols, sulfone and sulfinate reagents stand out versatile tools these reactions, particularly in mono-, di-, trifluoromethylations. Their versatility lies offering multiple pathways, encompassing electrophilic, nucleophilic, well radical mechanisms, thus providing diverse routes controlled molecular modifications through variety 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, ClSO2CH2F 2.4 PhSO2CH2F 3 Difluoromethylation 3.1 PhSO2CF2H 3.2 Benzothiazole-SO2CF2H 3.3 2-PyrSO2CF2H 3.4 NaSO2CF2H 4 Trifluoromethylation 4.1 PhSO2CF3 4.2 2-PyrSO2CF3 4.3 Benzothiazole-SO2CF3 4.4 NaSO2CF3 4.4.1 Electrochemical Approaches 4.4.2 Photochemical 4.4.3 Other Noteworthy 5 Conclusion

Language: Английский

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis DOI Creative Commons
Peng Wu,

Gabriel Goujon,

Shulei Pan

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(51)

Published: Sept. 5, 2024

Benzo[1,3,2]dithiazole-1,1,3-trioxides are bench-stable and easy-to-use reagents. In photoredox catalysis, they generate methyl perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, N-Ts acrylamide. As byproduct, salt is formed be regenerated the original methylating agent. Flow chemistry provides an option for reaction scale-up further underscoring synthetic usefulness these methylation Mechanistic investigations suggest single-electron transfer (SET) pathway induced by catalysis.

Language: Английский

Citations

2
Photocatalyzed Imino-Difluoromethylation of Alkenes with Bifunctional Oxime Esters DOI
Zhiwei Chen, Shuhang Yang, Liping Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13585 - 13594

Published: Sept. 11, 2024

Herein, we report a simple and versatile difluoromethylene-imide reaction in which series of olefins can undergo difluoromethylenimine under photocatalytic conditions through an energy transfer (EnT) process. The has mild wide range applicability. We successfully synthesized 27 molecules containing difluoromethylene units, featuring easily accessible starting materials operational simplicity.

Language: Английский

Citations

2
Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations DOI
G. K. Surya Prakash, Alexander Knieb

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 5, 2024

Abstract Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among established fluoroalkylation protocols, sulfone and sulfinate reagents stand out versatile tools these reactions, particularly in mono-, di-, trifluoromethylations. Their versatility lies offering multiple pathways, encompassing electrophilic, nucleophilic, well radical mechanisms, thus providing diverse routes controlled molecular modifications through variety 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, ClSO2CH2F 2.4 PhSO2CH2F 3 Difluoromethylation 3.1 PhSO2CF2H 3.2 Benzothiazole-SO2CF2H 3.3 2-PyrSO2CF2H 3.4 NaSO2CF2H 4 Trifluoromethylation 4.1 PhSO2CF3 4.2 2-PyrSO2CF3 4.3 Benzothiazole-SO2CF3 4.4 NaSO2CF3 4.4.1 Electrochemical Approaches 4.4.2 Photochemical 4.4.3 Other Noteworthy 5 Conclusion

Language: Английский

Citations

1