Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds DOI
Lin Tang, Zhen Yang,

Jingchao Jiao

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(16), P. 10449 - 10458

Published: July 23, 2019

By altering the amount of Selectfluor, highly selective mono- and difluorination 1,3-dicarbonyl compounds has been achieved, affording a variety 2-fluoro- 2,2-difluoro-1,3-dicarbonyl in good to excellent yields. The reaction can be readily performed aqueous media without any catalyst base, which features practical convenient fluorination. Importantly, gram-scale reaction, transformation 2-fluoro-1,3-diphenylpropane-1,3-dione 4-fluoro-1,3,5-triphenyl-1H-pyrazole, chlorination bromination are realized further exhibit its synthetic utility.

Language: Английский

Application of Bifunctional 2-Amino-1,4-naphthoquinones in Visible-Light-Promoted Photocatalyst-Free Alkene Perfluoroalkyl-Alkenylation DOI
Lin Tang, Fang Yang,

Zhen Yang

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 23(2), P. 519 - 524

Published: Dec. 31, 2020

A simple and practical photochemical strategy for intermolecular perfluoroalkyl-alkenylation of alkenes with 2-amino-1,4-naphthoquinones perfluoroalkyl iodides has been demonstrated under visible-light irradiation. Mechanistic studies reveal that easily available 2-amino-1,4-naphthoquinone substrates can serve as efficient photosensitizers to activate through a photoredox process. Therefore, the developed radical relay reaction proceeds smoothly without additional transition metals photocatalysts.

Language: Английский

Citations

32

Photoredox-catalyzed three-component carbotrifluoromethylation of alkenes via radical–radical cross-coupling DOI
Lin Tang,

Ge Lv,

Taijun Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4708 - 4715

Published: Jan. 1, 2024

A simple and practical visible light-driven photoredox-catalyzed three-component carbotrifluoromethylation of alkenes is revealed for the synthesis 1,4-bis(trifluoromethylated) compounds.

Language: Английский

Citations

3

Metal‐Free Promoted CF2/CF3‐Difunctionalization of Unactivated Alkenes DOI
Ming Li, Xinyu Zhu, Yi‐Feng Qiu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(12), P. 2945 - 2950

Published: March 28, 2019

Abstract An operationally simple radical difluoroalkylation/trifluoromethylation and alkynylation of unactivated alkenes under mild conditions has been developed. Through this protocol, a series CF 2 /CF 3 ‐ substituted linear alkynyl ketones were synthesized via unique 1,2‐alkynyl migration. Notably, no transition‐ metal catalyst is needed in the developed reaction system, excellent functional group compatibility was observed. magnified image

Language: Английский

Citations

29

PPh3/Selectfluor‐Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis DOI

Zhen Yang,

Siwei Chen, Fang Yang

et al.

European Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 2019(34), P. 5998 - 6002

Published: July 31, 2019

By taking the advantage of PPh 3 /Selectfluor system, carboxylic acids are efficiently converted into pivotal intermediates acyloxyphosphonium ions that can selectively react with a second acid or fluoride to in situ yield corresponding anhydrides acyl fluorides. The developed protocol features commercially availabile reagents, no involvement base, room temperature conditions, and simple experimental procedure. Additionally, various amides esters readily achieved, respectively, addition amines alcohols.

Language: Английский

Citations

29

Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds DOI
Lin Tang, Zhen Yang,

Jingchao Jiao

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(16), P. 10449 - 10458

Published: July 23, 2019

By altering the amount of Selectfluor, highly selective mono- and difluorination 1,3-dicarbonyl compounds has been achieved, affording a variety 2-fluoro- 2,2-difluoro-1,3-dicarbonyl in good to excellent yields. The reaction can be readily performed aqueous media without any catalyst base, which features practical convenient fluorination. Importantly, gram-scale reaction, transformation 2-fluoro-1,3-diphenylpropane-1,3-dione 4-fluoro-1,3,5-triphenyl-1H-pyrazole, chlorination bromination are realized further exhibit its synthetic utility.

Language: Английский

Citations

27