Substituent-Controlled Copper-Catalyzed Trifluoromethylation of 1,7-Dienes: Synthesis of Mono- and Bis-trifluoromethylated Benzoxepines DOI
Xiaowei Zhao, Xiang Gao,

Fangli Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7261 - 7266

Published: Aug. 21, 2024

A copper-catalyzed trifluoromethylation of benzene-linked 1,7-dienes with 1-trifluoromethyl-1,2-benziodoxole via a radical cascade cyclization process for the synthesis mono- and bis-trifluoromethylated benzoxepines is developed. The selectivity depends on substituents double bond allyl group in 1,7-dienes. large-scale operation late-stage functionalization bioactive molecules reveal promising utility this protocol.

Language: Английский

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

9
Electrochemical Multicomponent Cascade Radical Process Enabling Synthesis of Iodomethyl Spiropyrrolidinyl‐Oxindoles DOI

Jingrui He,

Haibo Mei, Jorge Escorihuela

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1691 - 1698

Published: March 19, 2024

Comprehensive Summary A novel electrochemical multicomponent cascade reaction of indole‐tethered alkenes with CF 3 SO 2 Na and n ‐Bu 4 NI has been developed, which enables the rapid assembly spiropyrrolidinyl‐oxindoles in good yields. The experimental results DFT calculations suggest that this proceeds through oxidation Na, radical coupling alkene, spirocyclization, sulfinate, iodide substitution, water coupling. This strategy features mild conditions, easy‐to‐handle reactants, chemical finding not only enriches research contents but also provides a green for construction compared existing methodologies.

Language: Английский

Citations

9
Mediator-free electrochemical trifluoromethylation: a cascade approach for the synthesis of trifluoromethylated isoxazolines DOI
Kingshuk Mahanty, Suman Kumar Saha, Atreyee Halder

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(30), P. 4467 - 4470

Published: Jan. 1, 2023

The developed methodology describes an environmentally benign protocol for electro-oxidative CF3-radical generation, followed by cascade cyclization fabricating isoxazoline scaffold from a β,γ-unsaturated oxime. Consecutive C-O and C-C bond formations were achieved through this method featuring mild, robust, scalable reaction conditions broad substrate scope. Mechanistic studies revealed the necessity of anodic oxidation process. Further conversion afforded other valuable derivatives.

Language: Английский

Citations

17
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
Visible-Light-Induced Trifluoromethyl Radical Addition to Thiocarbonyl of Thioamide Derivatives DOI

Yuanyuan Ren,

Yuxiu Zhou,

Ke‐Hu Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

An effective trifluoromethyl radical addition to the thiocarbonyl of thioamide derivatives is described, which produces various trifluoromethylthiolated N-heterocycles such as 6-(trifluoromethylthio)phenanthridine, 2-(trifluoromethylthio)indole, and 2-(trifluoromethylthio)benzothiazole under visible-light irradiation. The process features advantages mild reaction conditions, a cheap easily available source (CF3Br), green energy, well broad substrate scope. mechanism investigated in detail, scale-up experiments are performed.

Language: Английский

Citations

0
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

3
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 of Alkynes: The Unique Role of DMSO as a Masking Auxiliary DOI Creative Commons
Ji‐Hoon Jang, Ho Seong Hwang,

Haeryeong Jeong

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An electrochemical trifluoromethylation method for terminal alkynes has been developed, facilitating the synthesis of CF 3 -alkynes with DMSO as a masking auxiliary.

Language: Английский

Citations

1
Substituent-Controlled Copper-Catalyzed Trifluoromethylation of 1,7-Dienes: Synthesis of Mono- and Bis-trifluoromethylated Benzoxepines DOI
Xiaowei Zhao, Xiang Gao,

Fangli Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7261 - 7266

Published: Aug. 21, 2024

A copper-catalyzed trifluoromethylation of benzene-linked 1,7-dienes with 1-trifluoromethyl-1,2-benziodoxole via a radical cascade cyclization process for the synthesis mono- and bis-trifluoromethylated benzoxepines is developed. The selectivity depends on substituents double bond allyl group in 1,7-dienes. large-scale operation late-stage functionalization bioactive molecules reveal promising utility this protocol.

Language: Английский

Citations

0