Electrochemical Decarboxylative Trifluoromethylation of Cinnamic Acids Revisited: A Combined Experimental and Computational Study DOI Open Access
Yoshihiko Yamamoto, Norihiko Goto, Takeshi Yasui

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

β-(Trifluoromethyl)styrenes are potentially useful building blocks for the synthesis of organofluorine compounds because their electron-deficient C=C double bonds can undergo diverse transformations. One most practical methods preparing β-(trifluoromethyl)styrenes is decarboxylative trifluoromethylation readily available cinnamic acid derivatives using Langlois reagent as a less expensive trifluoromethyl source. We revisited electrochemical to identify modified conditions that reduce loading without additional additives. The reaction mechanism was computationally investigated gain insight into dependence product yields on aryl terminal groups. synthetic utility obtained demonstrated by transformation 4-aryl-3-(trifluoromethyl)pyrrolidines.

Language: Английский

Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes DOI

Jiaqing Shao,

Jiang Liu, Haibo Mei

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: 173, P. 134467 - 134467

Published: Jan. 12, 2025

Language: Английский

Citations

1

Radical Three-Component Nitro Spiro-Cyclization of Unsaturated Sulfonamides/Amides to Access NO2-Featured 4-Azaspiro[4.5]decanes DOI

Changyou Guo,

Li‐Jun Li,

Qinqin Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3069 - 3074

Published: April 1, 2024

Free radical three-component nitration/spirocyclization of unsaturated sulfonamides/amides with tert-butyl nitrite was developed for the construction diverse NO2-revised 4-azaspiro[4.5]decanes. This tandem system featured metal-free participation, simple operation, good selectivity/yields, and a green/low-cost O source. Meanwhile, one nitro-containing complex molecule scaled-up operation were performed well to test synthetic potential cascade reaction. Isotopic labeling, inhibition experiments, DFT analysis carried out gain insight into reaction process.

Language: Английский

Citations

6

Electrochemical Trifluoromethylation/Bicyclization of N-Cyanamide Alkenes: Synthesis of Bicyclic Amidine Derivatives DOI

Zhi-Hua Yan,

Yan Yan, Zhonglin Wei

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2718 - 2725

Published: Feb. 2, 2024

An anodically oxidizing trifluoromethylation cascade of N-cyanamide alkene bearing two electronically differentiated olefin moieties was reported, in which various N-unsaturated acyl cyanamide alkenes and CF3SO2Na acting as readily available starting materials furnished nonaromatic fused azaheterobicyclic compounds a highly efficient sustainable manner. The broad substrate scope, facile scalability, sustainability enabled this electrochemical process to be an appealing complement for trifluoromethylated cyclic amidines.

Language: Английский

Citations

4

Electrochemical direct α-amidation and α-pyrazolation of N-alkoxy- and N-aryloxycarbonyl pyrrolidines DOI

Zhuang Wang,

Yuxiu Liu, Hongjian Song

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(12), P. 7419 - 7423

Published: Jan. 1, 2024

We have developed a straightforward electrochemical protocol for direct α-amidation and α-pyrazolation of N -alkoxy- -aryloxycarbonyl pyrrolidines with amides or pyrazoles.

Language: Английский

Citations

4

Electrochemical Synthesis of Vinyl Sulfonates Mediated by Bromine Radicals DOI
Yong Huang, Yuyuan Zhang, Yujing Zhou

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

Vinyl sulfonates are vital intermediates in organic synthesis, serving as versatile electrophiles various cross-coupling reactions. Despite their significance, direct methods for synthesizing vinyl from styrenes have been limited. In this study, we introduce an innovative electrochemical approach that leverages bromine radical mediation to facilitate the synthesis of sulfonates, cheap nBu4NBr acts both electrolyte and a catalytic amount. This process involves reaction with sodium sulfinates water under conditions, offering straightforward pathway these compounds. The developed strategy is characterized by its high efficiency, operational simplicity, environmentally benign nature, adhering principles green chemistry while ensuring atom economy remarkable regioselectivity. Furthermore, methodology proves effective gram-scale allows subsequent functionalization sulfonate products pharmaceutical derivatives, thus broadening potential applications techniques styrene functionalization.

Language: Английский

Citations

0

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

Oxidative Aminotrifluoromethylation of 1,4-Naphthoquinone DOI
Lin Tang,

Fengjuan Jia,

Ruijun Yu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13117 - 13127

Published: Sept. 3, 2024

A strategy for convenient and precise oxidative aminotrifluoromethylation of 1,4-naphthoquinone with the Togni reagent amines has been demonstrated via a radical process. This method allows efficient access preparation wide range CF

Language: Английский

Citations

2

Electrochemical Trifluoromethylation/Spirocyclization of N-Benzylacrylamides to Construct Trifluoromethylated 2-Azaspiro[4.5]decanes DOI
Zhou Lan, Hong He,

De-Qiao Yang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 981 - 981

Published: Jan. 1, 2024

Language: Английский

Citations

1

Electrochemical synthesis of β-difluoromethylamide compounds by N-benzenesulfonylacrylamide with difluorine reagents DOI

Zhi-Long Lei,

Zong‐Cang Ding,

Shu‐Hui Li

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(59), P. 7614 - 7617

Published: Jan. 1, 2024

A mild and efficient electrochemical method for radical addition, cyclization, migration reaction was described in this work. difluoromethyl produced by anodizing CF

Language: Английский

Citations

1

Direct N H heteroarylation of NH-sulfoximines under electrochemical conditions DOI
Changsheng Qin, Jingfang Wang,

Fang Gao

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 568, P. 114485 - 114485

Published: Aug. 27, 2024

Language: Английский

Citations

0