General Defluoroalkylation of Trifluoromethylarenes with Both Electron-Donating and -Withdrawing Alkenes DOI
Mengqi Zhu, Qiaolin Wang, Huawen Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12591 - 12609

Published: Aug. 14, 2024

The incorporation of gem-difluoromethylene units into organic molecules remains a formidable challenge. Conventional methodologies for constructing aryldifluoromethyl derivatives relied on the use high-functional fluorinating regents under harsh conditions. Herein, we report general and efficient photoredox catalytic systems defluoroalkylation readily available trifluoromethylarenes through selective C–F cleavage to deliver gem-difluoromethyl radicals which proceed reductive addition both electron-donating withdrawing alkenes transition-metal free Mechanistic studies reveal that thiol serves as photocatalyst HAT reagent visible light irradiation. This synergistic photocatalysis catalysis protocol exhibits ample salient features such high chemo- regioselectivity, broad substrate scope, amenable gram-scale synthesis late-stage modification bioactive molecules.

Language: Английский

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

0
General Defluoroalkylation of Trifluoromethylarenes with Both Electron-Donating and -Withdrawing Alkenes DOI
Mengqi Zhu, Qiaolin Wang, Huawen Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12591 - 12609

Published: Aug. 14, 2024

The incorporation of gem-difluoromethylene units into organic molecules remains a formidable challenge. Conventional methodologies for constructing aryldifluoromethyl derivatives relied on the use high-functional fluorinating regents under harsh conditions. Herein, we report general and efficient photoredox catalytic systems defluoroalkylation readily available trifluoromethylarenes through selective C–F cleavage to deliver gem-difluoromethyl radicals which proceed reductive addition both electron-donating withdrawing alkenes transition-metal free Mechanistic studies reveal that thiol serves as photocatalyst HAT reagent visible light irradiation. This synergistic photocatalysis catalysis protocol exhibits ample salient features such high chemo- regioselectivity, broad substrate scope, amenable gram-scale synthesis late-stage modification bioactive molecules.

Language: Английский

Citations

2