Synthesis of N-Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate DOI

Yuhao Ding,

Yaopeng Liu,

Jin Ge

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12255 - 12262

Published: Aug. 16, 2024

An efficient p-TsOH-mediated insertion of sodium thiocyanate into trifluoromethylimidoyl sulfoxonium ylides has been reported, affording annulated N-aryl-4-trifluoromethylthiazol-2-amines in 42–84% yields a one-pot manner. This protocol encompasses variety with serving as the source "S–C═N" moiety thiazole ring. The versatile transformations resulting pharmacologically important were also demonstrated.

Language: Английский

Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks DOI

Yaopeng Liu,

Qingyu Tian,

Jin Ge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Language: Английский

Citations

12
Visible‐Light‐Driven Multicomponent Reactions of Diazosulfonium Triflates with Amines and CS2 or CO2: Direct Synthesis of Bis‐Dithiocarbamates/Carbamates DOI

Xue‐Cen Xu,

Yue‐Gong,

Jie Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

Comprehensive Summary Visible light‐induced transformation of CO 2 and CS into value‐added products has attracted worldwide attention because it mimics nature. In this context, although visible‐light‐induced direct synthesis dithiocarbamates carbamates employing SO as a C1 source been reported, all these reactions are limited to the preparation S ‐alkyl mono‐dithiocarbamates O mono‐carbamates. Herein, we report visible‐light photoredox‐catalyzed multicomponent reaction diazosulfonium triflates with amines or . Mechanistic studies indicate that diazomethyl radicals might be generated key intermediates, thus providing direction for application other radical acceptors.

Language: Английский

Citations

0
Base-Mediated Cyclization of N-Benzyl Ketimines with Vinyl Sulfoxides: An Approach to Polysubstituted 1-Pyrrolines DOI

Tenglong Xu,

Donghao Wang, Zhen Liang

et al.

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

Published: May 29, 2025

A protocol for synthesizing polysubstituted 1-pyrrolines (3,4-dihydro-2H-pyrrole) via base-mediated [3 + 2] cycloaddition of vinyl sulfoxides with N-benzyl ketimines under mild conditions has been developed. The methodology exhibits exceptional functional group compatibility, demonstrating applicability to both terminal and internal sulfoxide substrates. Control experiments 1H NMR analyses have conducted propose a plausible reaction pathway. synthetic value this strategy further validated through successful gram-scale synthesis subsequent transformation the products into diverse derivatives.

Language: Английский

Citations

0
Divergent Reactivity of Iminyl Radicals in Four Interrupted Pathways for the Synthesis of Cyclic/Acyclic Ketones and N-Heterocycles from Vinyl Azides and Phenylacetic Acids DOI

Swagota Paul,

A. K. BARUAH,

Atul A. More

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13128 - 13136

Published: Sept. 11, 2024

Herein, we report the Ag-catalyzed substrate-controlled interrupted radical pathways of iminyl radical. The benzylic groups played a crucial role in pathway selection involving series dimerization and hydrolysis, 1,5-H shift followed by cascade cyclization, direct N-(sp

Language: Английский

Citations

1
Dual Photoredox/Copper-Catalyzed Three-Component Alkylcyanation of Alkenes and 1,4-Alkylcyanation of 1,3-Enynes Employing Sulfoxonium Ylides as the Carbon Radical Precursors DOI
Zixuan Yang,

Xue‐Cen Xu,

Bowen He

et al.

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

Published: Dec. 3, 2024

A novel dual photoredox/copper-catalyzed three-component alkylcyanation of alkenes and 1,4-alkylcyanation 1,3-enynes have been developed. In this radical cyanoalkylation reaction, the photoredox induced alkyl from sulfoxonium ylides adds to carbon-carbon double bonds styrenes or 1,3-enynes, generated benzylic allenyl radicals couple with a Cu(II) cyanide complex achieve selective cyanation. The reaction exhibits high chemo- regioselectivity wide substrate scope, providing an efficient method for synthesis nitriles in single step.

Language: Английский

Citations

1
Synthesis of N-Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate DOI

Yuhao Ding,

Yaopeng Liu,

Jin Ge

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12255 - 12262

Published: Aug. 16, 2024

An efficient p-TsOH-mediated insertion of sodium thiocyanate into trifluoromethylimidoyl sulfoxonium ylides has been reported, affording annulated N-aryl-4-trifluoromethylthiazol-2-amines in 42–84% yields a one-pot manner. This protocol encompasses variety with serving as the source "S–C═N" moiety thiazole ring. The versatile transformations resulting pharmacologically important were also demonstrated.

Language: Английский

Citations

0