Cited by Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4H-benzo[4,5]imidazo[2,1-b][1,3]thiazine

Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis DOI

Ya-Fei Hu,

Wei Han,

Ye-Kun Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5144 - 5150

Published: Jan. 1, 2024

A transition-metal-free multi-functionalization reaction of β-trifluoromethyl enones and azacycles is first developed for the synthesis valuable amino-2,3-dihydrofuran derivatives.

Language: Английский

Citations

Defluorinative functionalization of perfluoroalkyl alkenes with ureas: synthesis of C4-perfluoroalkenyl 2-imidazolones DOI

Wei Han,

Ming-Yao Tang,

Y. Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5538 - 5544

Published: Jan. 1, 2024

A defluorinative 1,2,3,4-tetrafunctionalization of perfluoroalkyl alkenes with readily available ureas via multi-bond interconversion at four carbon sites has been developed for the synthesis perfluoroalkenyl 2-imidazolones.

Language: Английский

Citations

Mild [3 + 3] Annulation of (Trifluoromethyl)alkenes with Thioureas Enabled by Chemoselective Defluorinative Amination: Synthesis of 6-Fluoro-3,4-dihydropyrimidine-2(1H)-thiones DOI

Rongbin Peng,

Chuanle Zhu

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1538 - 1548

Published: Jan. 21, 2025

The chemoselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes with thioureas is reported. This protocol affords various attractive 6-fluoro-3,4-dihydropyrimidine-2(1H)-thiones in high yields, features transition-metal free, mild conditions, efficient, operationally simple and gram-scalable, tolerates diverse useful functional groups.

Language: Английский

Citations

Modular Synthesis of Monofluorinated 1,2,4-Triazoles/1,3,5-Triazines via Defluorinative Annulations of N-CF₃ Imidoyl Chlorides DOI

Chi Gao,

Ru Zhong Zhang,

Mang Wang

et al.

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

Published: March 10, 2025

Ring-fluorinated azaheterocycles have wide applications in agrochemicals, pharmaceuticals, and synthesis, which prompt continuous endeavors to expand such heterocyclic families. However, monofluorinated triazaheterocycles hardly been explored. This work reported a novel modular synthesis of 1,2,4-triazoles 1,3,5-triazines, utilizes N-CF3 imidoyl chlorides as unique polyfluoro synthons their defluorinative annulations with hydrazines/imidazines. Further modifications these fluorinated heterocycles highlight the potential method for accessing functional molecules.

Language: Английский

Citations

Photocatalyzed/Base-Mediated Defluorinative Three-Component Cascade Cyclization: Access to Monofluorocyclohexenes and 6-Fluoro-1,2,3,4-tetrahydropyridines DOI

Shuyue Zhang,

Meixue Gan,

Fan Zhang

et al.

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

Published: March 19, 2025

A three-component cascade cyclization of α-CF3 alkenes, electron-rich and dimethyl esters or sulfonamides via a dual C–F bond cleavage process is described. This methodology provides general efficient strategy to access monofluorocyclohexenes 6-fluoro-1,2,3,4-tetrahydropyridines by switching the bifunctional reagents (dimethyl sulfonamides), which are valuable building blocks in synthetic chemistry pharmaceutical industries. The reaction mechanism applications products have been demonstrated.

Language: Английский

Citations

Regioselective difluoroallylation of alkylidene malonates with trifluoromethyl alkenes: synthesis of gem-difluoro-1,5-dienes and their [2 + 2] photocycloaddition DOI

Weidi Zeng, Mingqiang Li,

Shaofeng Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3421 - 3426

Published: Jan. 1, 2024

The synthesis of gem -difluoro-1,5-dienes via regioselective S N 2′-type reactions alkylidene malonates with trifluoromethyl alkenes and their subsequent [2 + 2] photocycloaddition for the formation bicyclo[2.1.1]hexanes are described.

Language: Английский

Citations

Photoredox Catalyzed Synthesis of gem-Difluoroalkenes and Monofluorinated Cyclooctenes via 1,5-HAT Process DOI

Yuanbo Li, Yu‐Lin Wang,

Qian Gao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4548 - 4553

Published: May 17, 2024

gem-Difluoroalkenes and monofluorinated cycloalkenes have emerged as basic structural units in a variety of bioactive molecules natural products. Thus, developing straightforward efficient methods for synthesizing fluorinated alkene compounds is considerable significance. Herein, we disclose visible-light-induced defluorination 2-trifluoromethyl-1-alkene via 1,5-HAT process using N-alkoxyphtalimides both radical precursor potential nucleophile. The mild stepwise reaction leads to structurally diverse gem-difluoroalkenes cyclooctenes with high efficiency, respectively.

Language: Английский

Citations

Base-Mediated Regioselective [3 + 3] Annulation of Alkylidene Malononitriles with Trifluoromethyl Alkenes via Dual C–F Bond Cleavage DOI

Mingqiang Li, Weidi Zeng,

Ablimit Abdukader

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7452 - 7456

Published: Aug. 26, 2024

A base-mediated regioselective [3 + 3] annulation of alkylidene malononitriles with trifluoromethyl alkenes was described. The reaction proceeds through sequential intermolecular SN2′ and intramolecular SNV-type cyclization by cleaving dual C–F bonds in a group, which discriminate multiple carbon-nucleophilic sites using single base. Various bicycles bearing monofluorocyclohexene motif were assembled from readily available starting materials under mild conditions via one-pot cascade approach.

Language: Английский

Citations

Divergent Synthesis of Benzo[4,5]imidazo[2,1-b][1,3]thiazines and α-Trifluoromethyl-β-arylthio Tertiary Alcohols from 2-Mercaptobenzimidazoles and α-CF₃ Alkenes DOI

Bin Wang,

Hua Kuan Lin,

Ziren Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9610 - 9616

Published: Oct. 25, 2024

An efficient and metal-free approach for the divergent synthesis of 2-fluoro-3-aryl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines α-trifluoromethyl-β-arylthio tertiary alcohols from 2-mercaptoimidazoles α-CF3 alkenes has been developed. The chemoselectivity was well controlled by base or light; a series were afforded via base-mediated sequential SN2′- SNV-type reactions. Meanwhile, could be selectively achieved through visible-light-driven electron donor–acceptor (EDA) complex-initiated radical cascade thiolation/hydroxylation in absence base, transition metal, external photocatalyst.

Language: Английский

Citations

Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4H-benzo[4,5]imidazo[2,1-b][1,3]thiazine DOI

Yupian Deng,

Yuhao Qian,

Jia‐Qi Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

A base-controlled synthesis of N -β-CF 3 -substituted 2 H -benzo[ d ]imidazole-2-thiones and 2-fluoro-4 -benzo[4,5]imidazo[2,1- b ][1,3]thiazines via hydroamination or defluorinative cyclizations α-CF -styrenes with 2-mercaptobenzimidazole was developed.

Language: Английский

Citations