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

Recent advances in N-heterocyclic carbene (NHC)-catalyzed fluorination and fluoroalkylation DOI

Zefeng Jin,

Fuxiang Zhang, Xiao Xiao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2112 - 2133

Published: Jan. 1, 2024

Organofluorine compounds are of high value. NHC-catalyzed fluorination and fluoroalkylation have served as powerful versatile vehicles for accessing the related organofluorines. This review focuses on recent developments in this area.

Language: Английский

Citations

29

Photoredox/NHC cooperative catalysis for alkylacylation of styrenes: An alternative method for the synthesis of γ-aminoketones DOI

Ke-Yang Yu,

Fu Cheng,

Dong-Sen Duan

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 156, P. 155450 - 155450

Published: Jan. 8, 2025

Language: Английский

Citations

1

N-monofluoromethoxy benzoimidazole: a bench stable reagent for direct radical monofluoromethoxylation of alkenes DOI
Ning Chen, Jingjing Ling, Keguang Cheng

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 12, 2025

Language: Английский

Citations

1

NHC and photoredox catalysis dual-catalyzed 1,4-mono-/di-fluoromethylative acylation of 1,3-enynes DOI

Jiuli Xia,

Ruiyang Ma,

Lihong V. Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3089 - 3099

Published: Jan. 1, 2024

NHC and photocatalysis dual-catalyzed mono/difluoromethylative acylation of 1,3-enynes was realized, providing fluormethyl-substituted allenyl ketones. SO 2 might play a critical role in achieving high reactivity selectivity.

Language: Английский

Citations

5

Functionalization of 1,3‐Butadiene Derivatives under Photo/Electrocatalysis DOI

Yinghui Huang,

Linhui Shen,

Chunhua Ma

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(28)

Published: May 20, 2024

Abstract In recent years, the functionalization of 1,3‐butadiene has become an attractive strategy for constructing allyl compounds with molecular and structural complexity, current research focuses on synthetic chemistry organic synthesis. Compared traditional synthesis method, methods promoted by photochemistry or electrochemistry represent environmentally friendly mild strategy. this review, reactions under photochemical/electrochemical processes in years are reviewed according to classification systems, particular emphasis corresponding reaction mechanism, which lays a foundation further exploration new catalytic methods.

Language: Английский

Citations

5

Radical Acylfluoroalkylation of 1,3-Enynes via N-Heterocyclic Carbene/Photoredox Cooperative Catalysis DOI
Shichao Tian, Ning Chen, Keguang Cheng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4351 - 4355

Published: May 10, 2024

We report a novel three-component radical acylfluoroalkylation of 1,3-enynes by synergistic N-heterocyclic carbene (NHC)/photoredox catalysis toward various fluorinated allenic aryl ketones. This protocol features broad substrate scope and excellent functional group tolerability, with examples late-stage modification drug molecules natural products. Notably, seven different fluoroalkyl motifs can be introduced to 1,3-enynes, further demonstrating the robustness generality this method. The generation from each sulfinate reagent was individually supported EPR experiments.

Language: Английский

Citations

4

Visible Light-Mediated Monofluoromethylation/Acylation of Olefins by Dual Organo-Catalysis DOI Creative Commons

Jiuli Xia,

Yunliang Guo,

Zhiguang Lv

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(4), P. 790 - 790

Published: Feb. 8, 2024

Monofluoromethyl (CH2F) motifs exhibit unique bioactivities and are considered privileged units in drug discovery. The radical monofluoromethylative difunctionalization of alkenes stands out as an appealing approach to access CH2F-containing compounds. However, this strategy remains largely underdeveloped, particularly under metal-free conditions. In study, we report on visible light-mediated three-component monofluoromethylation/acylation styrene derivatives employing NHC organic photocatalyst dual catalysis. A diverse array α-aryl-β-monofluoromethyl ketones was successfully synthesized with excellent functional group tolerance selectivity. mild CH2F generation from NaSO2CFH2 holds potential for further applications fluoroalkyl chemistry.

Language: Английский

Citations

3

Recent progress in carbene-catalyzed fluoroalkylation DOI
Bei Zhang, Xuan Zhang, Jian Wang

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(8), P. 2448 - 2460

Published: June 26, 2024

Language: Английский

Citations

2

1,2-Amidoarylcarbonylation of Styrenes to Access β-Acylamino Ketones by NHC-Catalyzed Radical Relay DOI
Dengyu Yin,

Lishuai Lu,

Ying Jiang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13085 - 13092

Published: Aug. 28, 2024

An amidoarylcarbonylation reaction of aromatic aldehydes and olefins with Katritzky pyridinium salts by N-heterocyclic carbene (NHC)-catalyzed radical relay to construct C-C C-N bonds good functional group tolerance is developed for the synthesis β-acylamino ketones. This gentle efficient approach offers a valuable style Mechanistic studies revealed that addition/coupling/elimination cascade process was involved in this reaction.

Language: Английский

Citations

2

Photocatalytic Decarboxylative Fluoroalkylation of α,β‐Unsaturated Carboxylic Acids DOI Open Access

xiuling Wang,

Yaxing Wu,

Songlin Xu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract A decarboxylative fluoroalkylation of α,β‐unsaturated acids was developed by the use a dual nickel/photoredox catalysis system. The fluoroalkyl radicals are generated from α‐CF 3 alkyl bromides nickel‐induced single electron transfer (SET) and subsequently intercepted cinnamic acid to forge targeted C−C bonds. wide variety substrates bearing diverse set functional groups were compatible with mild reaction conditions (visible light, room temperature, cheap metal, no strong oxidant or reductant), thus affording trifluoromethyl analogues α‐methylated allylic compounds.

Language: Английский

Citations

2