N-heterocyclic carbene-catalyzed nucleophilic aromatic substitution reaction of polyfluoroarenes DOI

Lishuai Lu,

Dengyu Yin, Xiaoxuan Li

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(18), P. 1551 - 1563

Published: Aug. 28, 2024

Fluorinated asymmetric aryl ketones represent a pivotal class of organic synthesis intermediates, which have garnered widespread application in the realms chemistry, materials science, and drug discovery. Herein, we report pioneering nucleophilic aromatic substitution (SNAr) reaction involving aldehydes polyfluoroarenes, elegantly catalyzed by N-heterocyclic carbene (NHC). This innovative strategy yields bis(hetero)aryl ketone products ranging from moderate to exceptional (40–83%), all achieved under gentle conditions, devoid both transition metals directing groups. The versatility this method is underscored its compatibility with broad spectrum substrates, particularly exhibiting remarkable resilience toward alkoxy functional Notably, successfully transformed an array biologically active molecules, crafting series their corresponding derivatives precision.

Language: Английский

Investigation of the reaction of hexafluoro-1,4-naphthoquinone with substituted phenols DOI
Ekaterina Kudryavtseva, Boris V. Lichitsky, E.V. Tretyakov

et al.

Journal of Fluorine Chemistry, Journal Year: 2025, Volume and Issue: 282, P. 110402 - 110402

Published: Feb. 1, 2025

Language: Английский

Citations

0
Light-Driven N-Heterocyclic Carbene-Catalyzed Multi-Component Reaction for the Synthesis of β-Amino Ketones DOI
Chengcheng Shi,

Nan Zhong,

Lin Guo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8848 - 8853

Published: Oct. 8, 2024

A N-heterocyclic carbene-catalyzed (NHC) three-component reaction involving

Language: Английский

Citations

2
Synthesis of Substituted N'‐(3,5,6,7,8‐Pentafluoro‐1,4‐Dioxo‐1,4‐Dihydronaphthalen‐2‐yl)Hydrazides by Condensation of Acyl Hydrazines and Perfluoro‐1,4‐Naphthoquinone DOI
Ekaterina Kudryavtseva, Boris V. Lichitsky, E.V. Tretyakov

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(43)

Published: Nov. 1, 2024

Abstract The reaction of different acyl hydrazines with hexafluoro‐1,4‐napthoquinone was studied for the first time. It demonstrated that this interaction stops at substitution one fluorine atom in quinone moiety. Based on observed reaction, a general approach to synthesis pentafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl hydrazides developed. revealed optimal conditions condensation are reflux MeOH 0.25 h; note, protocol does not require any chromatographic purification target products. method is versatile and makes it possible prepare products containing various substituents aryl part molecule. In addition, alkyl heteroaryl can be employed as starting compounds too, presence hydroxy cyano groups applied interfere condensation. structure obtained products, namely 4‐chloro‐N□‐(3,5,6,7,8‐pentafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)benzohydrazide, confirmed by X‐ray diffraction. crystals hydrazide, both NH form intermolecular hydrogen bonds give rise layers lying [001] plane. Prepared N'‐(3,5,6,7,8‐pentafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)hydrazides interest redox‐active ligands precursors obtaining wide range functionalized 1,4‐napthoquinones medicine chemistry.

Language: Английский

Citations

2
N-heterocyclic carbene-catalyzed nucleophilic aromatic substitution reaction of polyfluoroarenes DOI

Lishuai Lu,

Dengyu Yin, Xiaoxuan Li

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(18), P. 1551 - 1563

Published: Aug. 28, 2024

Fluorinated asymmetric aryl ketones represent a pivotal class of organic synthesis intermediates, which have garnered widespread application in the realms chemistry, materials science, and drug discovery. Herein, we report pioneering nucleophilic aromatic substitution (SNAr) reaction involving aldehydes polyfluoroarenes, elegantly catalyzed by N-heterocyclic carbene (NHC). This innovative strategy yields bis(hetero)aryl ketone products ranging from moderate to exceptional (40–83%), all achieved under gentle conditions, devoid both transition metals directing groups. The versatility this method is underscored its compatibility with broad spectrum substrates, particularly exhibiting remarkable resilience toward alkoxy functional Notably, successfully transformed an array biologically active molecules, crafting series their corresponding derivatives precision.

Language: Английский

Citations

0