Flow Chemistry of Metal Carbenoid Species towards Selective Organic Synthesis DOI
Kazuhiro Okamoto, Aiichiro Nagaki

Synthesis, Journal Year: 2024, Volume and Issue: 56(18), P. 2899 - 2908

Published: April 9, 2024

Abstract This review deals with C1 carbenoid chemistry, a focus on lithium species generated in flash flow systems. Strict control of the temperature, residence time, and mixing efficiency has led to various transformation reactions involving epoxidation, cyclopropanation, homologation, among others. The use other metal species, including trifluoromethylpotassium (CF3K) magnesium/ zinc carbenoids, systems is also introduced. 1 Introduction 1.1 Lithium Carbenoids Chemistry 1.2 Flow for 2 Reactions Involving Carbenoid Species 2.1 Deprotonative Generation 2.2 via Halogen–Lithium Exchange 2.3 Reductive Lithiation 2.4 Alkyllithiation 2.5 Trifluoromethylpotassium 2.6 Other Metal 3 Conclusion

Language: Английский

Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans DOI
Chun‐Yan Wu, Xiang‐Long Chen, Dongsheng Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4

Language: Английский

Citations

2

Efficiently nucleophilic trifluoromethylation of aldehydes over MgSO4/ZrO2 catalyst DOI
Weitao Wang, Yan Geng, Huan Wang

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 556, P. 113948 - 113948

Published: Feb. 16, 2024

Language: Английский

Citations

1

Efficient Trifluoromethylation of Halogenated Hydrocarbons Using Novel [(bpy)Cu(O2CCF2SO2F)2] Reagent DOI Creative Commons

Xiong Wu,

Xin Qiu,

Wenrun Lou

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2849 - 2849

Published: June 14, 2024

This study introduces a novel trifluoromethylating reagent, [(bpy)Cu(O2CCF2SO2F)2], notable for not only its practical synthesis from cost-effective starting materials and scalability but also nonhygroscopic nature. The reagent demonstrates high efficiency in facilitating trifluoromethylation reactions with various halogenated hydrocarbons, yielding products good yields exhibiting broad functional group compatibility. development of [(bpy)Cu(O2CCF2SO2F)2] represents an advancement the field organic synthesis, potentially serving as valuable addition to arsenal existing agents.

Language: Английский

Citations

1

A Continuous Flow Process for the Defluorosilylation of HFC-23 and HFO-1234yf DOI Creative Commons

S Patrick,

James A. Bull,

Philip L. Miller

et al.

Published: Aug. 30, 2024

A continuous flow process has been developed for the defluorosilylation of trifluoromethane (HFC-23) and 2,3,3,3-propene (HFO-1234yf) through reaction with lithium silanide reagents under inert conditions. Design experiment optimization improved conditions including productivity, yields, reduction solvent use, gas destruction. The small chain fluorinated organosilane products R3SiCF2H R3SiCH2C(F)=CF2 were competent nucleophiles in fluoride-catalyzed difluoromethylation aldehydes, trifluoroallylation ketones, imines. Stepwise treatment KHMDS IPrCuCl gave IPrCuCC–CF2H, which reacted allyl acyl halides to transfer propyne motif.

Language: Английский

Citations

1

A Continuous Flow Process for the Defluorosilylation of HFC-23 and HFO-1234yf DOI Creative Commons

S Patrick,

James A. Bull, Philip W. Miller

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 1, 2024

A continuous flow process has been developed for the defluorosilylation of trifluoromethane (HFC-23) and 2,3,3,3-tetrafluoropropene (HFO-1234yf) through reaction with lithium silanide reagents under inert conditions. Design experiment optimization improved conditions, including productivity, yields, reduction solvent use, gas destruction. The small chain fluorinated organosilane products R

Language: Английский

Citations

1

Flow Chemistry of Metal Carbenoid Species towards Selective Organic Synthesis DOI
Kazuhiro Okamoto, Aiichiro Nagaki

Synthesis, Journal Year: 2024, Volume and Issue: 56(18), P. 2899 - 2908

Published: April 9, 2024

Abstract This review deals with C1 carbenoid chemistry, a focus on lithium species generated in flash flow systems. Strict control of the temperature, residence time, and mixing efficiency has led to various transformation reactions involving epoxidation, cyclopropanation, homologation, among others. The use other metal species, including trifluoromethylpotassium (CF3K) magnesium/ zinc carbenoids, systems is also introduced. 1 Introduction 1.1 Lithium Carbenoids Chemistry 1.2 Flow for 2 Reactions Involving Carbenoid Species 2.1 Deprotonative Generation 2.2 via Halogen–Lithium Exchange 2.3 Reductive Lithiation 2.4 Alkyllithiation 2.5 Trifluoromethylpotassium 2.6 Other Metal 3 Conclusion

Language: Английский

Citations

0