Electrocatalysis Decarboxylative Annulation of Benzol[e][1,2,3]-oxathiazine-2,2-dioxides with N-Arylglycines DOI

Linheng He,

Wen Xia,

Yuxiang Zhou

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 997 - 997

Published: Jan. 1, 2024

Language: Английский

Electrochemical radical-polar crossover: a radical approach to polar chemistry DOI

Zhoumei Tan,

Haonan Zhang, Kun Xu

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 450 - 470

Published: Nov. 3, 2023

Language: Английский

Citations

50

Recent Advances in the Electrochemical Defluorinative Transformations of C—F Bonds DOI

Qinhui Wan,

Ruixue Liu, Zhongyi Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(16), P. 1913 - 1928

Published: April 24, 2024

Comprehensive Summary Organic fluorine compounds are ubiquitous and pivotally important organic molecules, yet their activation transformation have long been a formidable challenge due to the high energy low reactivity of C—F bonds. electrosynthesis, an environmentally benign synthetic method in chemistry, enables myriad chemical transformations without need for external redox reagents. In recent years, electrochemistry has emerged as powerful tool achieving bonds fluorine‐containing compounds. This review aims succinctly recapitulate latest advancements electrochemical defluorinative delve into reaction design, mechanistic insights, developmental prospects these methods. Key Scientists 1959, Lund was first pioneer electroreduction CF 3 CH group. Electrochemistry lately provided new opportunities efficient conversion fluorides. 2020, Zhou coworkers discovered carboxylation α‐CF alkenes. Lambert colleagues reported electrophotocatalytic amination aryl Electrochemical hydrodefluorination trifluoromethylketones developed by Lennox 2021. same year, Wang Guo disclosed radical alkylation alkenes with Katritzky salts alkyl precursors. Subsequently, Wu Liao described transition‐metal‐free, site‐selective arylation polyfluoroarenes (het)arenes using paired electrophotocatalysis. 2023, numerous efforts were made achieve bond activation. Xia organoboron‐controlled chemoselective sequential (deutero)hydrodefluorination trifluoroacetamides.

Language: Английский

Citations

26

Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3+OTf) as a Bifunctional Reagent DOI
Xiang Fang,

Dehui Wang,

Kun Xu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 411 - 415

Published: Dec. 26, 2023

We report a strategic exploitation of trifluoromethyl thianthrenium triflate (TT-CF3+OTf–) as both electromediator and CF3 radical precursors for paired electrolysis. Enabled by this strategy, the three-component trifluoromethylheteroaromatization alkenes alkynes was realized. The superiority TT-CF3+OTf– to other electrophilic reagents is attributed cathodic generation thianthrene (TT) mediator, which shifts heterogeneous oxidation interest homogeneous one.

Language: Английский

Citations

26

Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate DOI
Chang Ge,

Lipeng Qiao,

Yuyang Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1679 - 1685

Published: March 15, 2024

Comprehensive Summary A novel and eco‐friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF 3 + OTf − ) for trifluoromethylation imidazole‐fused heteroaromatic compounds was established. This method involves the direct electrolysis TT–CF without requirement external oxidants or catalysts, aligning with principles green chemistry. wide range including imidazo[1,2‐ a ]pyridines benzo[ d ]imidazo[2,1‐ b ]thiazoles have been successfully trifluoromethylated using this technique, exhibiting excellent compatibility various functional groups broad substrate scope. Moreover, method's applicability one‐pot sequential reactions enables reduction waste resource consumption by eliminating need intermediate purification steps.

Language: Английский

Citations

10

Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes DOI

Kaixing Gong,

Yingchun Ma,

Ping Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2352 - 2362

Published: April 5, 2024

Abstract While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well one with low loading is presented. These external‐oxidant‐free cyclizations are enabling applicable to range activated alkenes, affording diverse array thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐ ]isoquinolin‐6(5 H )‐ones, benzoimidazo[2,1‐ )‐ones indolin‐2‐ones, protocols amenable late‐stage diversification complex molecular architectures gram‐scale syntheses. Sunlight could serve light source, be conducted in an all‐solar‐driven mode using commercially available photovoltaic panel produce electricity.

Language: Английский

Citations

9

Electro-reductive carboxylation of C Cl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO2 DOI
Li Li, Zhi-xin Yan,

Chuan‐Kun Ran

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(12), P. 110104 - 110104

Published: June 8, 2024

Language: Английский

Citations

9

An electrocatalytic mono-functionalization of alkenes towards alkenyl selenium sulfonates DOI

Zhiheng Zhao,

Hongyan Yan,

Lijun Gu

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

In this study, a straightforward and environmentally benign electrochemical mono-functionalization of alkenes has been established for the synthesis alkenyl selenium sulfonates using elemental as source.

Language: Английский

Citations

1

An electrochemical-enabled cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles DOI
Dandan Li, Long Chen,

Yang Jin

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(12), P. 4656 - 4661

Published: Jan. 1, 2023

An electrochemical-enabled three-component cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles has been developed under external oxidant-free conditions.

Language: Английский

Citations

20

Recent advances in paired electrolysis and their application in organic electrosynthesis DOI
Gerhard Hilt

Current Opinion in Electrochemistry, Journal Year: 2023, Volume and Issue: 43, P. 101425 - 101425

Published: Nov. 20, 2023

Language: Английский

Citations

16

Electrochemical umpolung of C‐H nucleophiles bearing three electron‐withdrawing groups to trigger radical 1,2‐alkylarylations of allylic alcohols DOI Open Access
Qibin Li, Die Hu, Kun Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Abstract The electrochemical catalyst‐free generation of carbon radicals bearing three electron‐withdrawing groups from the corresponding C−H nucleophiles remains unexplored. To this end, we report a direct electro‐oxidation strategy to access these electrophilic under conditions. Enabled by strategy, radical 1,2‐alkylarylations allylic alcohols was realized, affording β ‐quaternary ketones with high functional group compatibility. This protocol is operationally simple and also easy scale up.

Language: Английский

Citations

0