Visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na leading to 3-trifluoroalkylated quinoxalin-2(1H)-ones

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 32(1), P. 258 - 262

Published: Nov. 20, 2020

Language: Английский

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Visible-light-initiated 4CzIPN catalyzed multi-component tandem reactions to assemble sulfonated quinoxalin-2(1H)-ones

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(3), P. 1479 - 1482

Published: Aug. 12, 2021

Language: Английский

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Functionalized quinoxalinones as privileged structures with broad-ranging pharmacological activities

European Journal of Medicinal Chemistry, Journal Year: 2022, Volume and Issue: 229, P. 114085 - 114085

Published: Jan. 1, 2022

Language: Английский

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Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 110112 - 110112

Published: June 25, 2024

Language: Английский

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Photoinduced Three-Component Difluoroalkylation of Quinoxalinones with Alkenes via Difluoroiodane(III) Reagents

Organic Letters, Journal Year: 2022, Volume and Issue: 24(19), P. 3576 - 3581

Published: May 12, 2022

An environmentally friendly strategy for the photocatalyzed three-component reaction between quinoxalinones, alkenes, and hypervalent iodine(III) reagents is disclosed. The new designed difluoroiodane(III) reagent shows excellent reactivity, providing a wide range of difluoroalkyl-substituted quinoxaline-2(1H)-ones in moderate to yields under mild conditions. Experimental studies demonstrated that difluoroalkyl radical intermediate was involved this reaction.

Language: Английский

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Three‐Component Reactions of Quinoxalin‐2(1H)‐ones: Recent Advances

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Sept. 11, 2023

Abstract The multicomponent reactions of quinoxalin‐2(1 H )‐ones has attracted considerable interest due to their significant biological and chemical activities. very recent advances (from 2021 the beginning 2023) on radical three‐component cascade reaction )‐one derivatives at C3 position were summarized in this mini‐review. According kind types involved, some representative examples detailed mechanism have been categorized discussed. red front was covered by Figure 1.

Language: Английский

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Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF₃⁺OTf^–) as a Bifunctional Reagent

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 411 - 415

Published: Dec. 26, 2023

We report a strategic exploitation of trifluoromethyl thianthrenium triflate (TT-CF3+OTf–) as both electromediator and CF3 radical precursors for paired electrolysis. Enabled by this strategy, the three-component trifluoromethylheteroaromatization alkenes alkynes was realized. The superiority TT-CF3+OTf– to other electrophilic reagents is attributed cathodic generation thianthrene (TT) mediator, which shifts heterogeneous oxidation interest homogeneous one.

Language: Английский

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Enantioselective Tsuji‐Trost α‐Fluoroallylation of Amino Acid Esters with Gem‐Difluorinated Cyclopropanes

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(23)

Published: Feb. 27, 2024

A novel enantioselective Tsuji-Trost-type cross coupling reaction between gem-difluorinated cyclopropanes and N-unprotected amino acid esters enabled by synergistic Pd/Ni/chiral aldehyde catalysis is presented herein. This transformation streamlined the diversity-oriented synthesis (DOS) of optically active α-quaternary α-amino bearing a linear 2-fluoroallylic motif, which served as an appealing platform for construction other valuable enantioenriched compounds. The key intermediates were confirmed HRMS detection, while DFT calculations revealed that excellent enantioselectivity was attributed to stabilizing non-covalent interactions Pd(II)-π-fluoroallyl species Ni(II)-Schiff base complex.

Language: Английский

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Diversity-oriented synthesis of fluoroalkylated amines via the palladium-catalyzed divergent fluoroalkylamination of 1,3-dienes

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(37), P. 5614 - 5617

Published: Jan. 1, 2022

Herein, we reported the first versatile and expeditious protocol for diversity-oriented synthesis (DOS) of fluoroalkylated amines via photoinduced palladium-catalyzed cross coupling 1,3-dienes, fluoroalkyl iodides, which features excellent 3,4- 1,4-selectivity controlled by a broad substrate scope as well good function group tolerance, could be extended to late-stage modification bioactive molecules.

Language: Английский

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Visible‐Light‐Driven Multicomponent Radical Cascade Versatile Alkylation of Quinoxalinones Enabled by Electron Donor Acceptor Complex in Water

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(7), P. 1020 - 1026

Published: March 10, 2023

Abstract An operationally simple aqueous phase three‐component photochemical strategy for the alkylation of quinoxalin‐2(1 H )‐ones with diethyl α ‐bromomalonate and unactivated alkenes in absence both photoredox catalysts additive has been developed. This reaction is driven by activity electron donor‐acceptor (EDA) complexes formed ‐bromomalonate. Irradiation visible light triggered single‐electron transfer (SET) from to ‐bromomalonate, inducing formation corresponding alkyl radical subsequent tandem reaction. It provides an efficient way construct alkylated quinoxalinones small molecules. magnified image

Language: Английский

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