Recent advances in the direct functionalization of quinoxalin-2(1H)-ones

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(24), P. 5863 - 5881

Published: Jan. 1, 2019

The direct C3-functionalization of quinoxalin-2(1H)-ones via C–H bond activation has recently attracted considerable attention, due to their diverse biological activities and chemical properties.

Language: Английский

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Visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids under metal-, strong oxidant- and external photocatalyst-free conditions

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(5), P. 1720 - 1725

Published: Jan. 1, 2020

An eco-friendly visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones and α-oxo carboxylic acids with air as the oxidant under external-photocatalyst-free conditions was established.

Language: Английский

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Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2021, Volume and Issue: 42(11), P. 1921 - 1943

Published: Aug. 30, 2021

Language: Английский

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Review and Theoretical Analysis of Fluorinated Radicals in Direct C_Ar−H Functionalization of (Hetero)arenes

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(16)

Published: Jan. 29, 2024

Abstract We highlight key contributions in the field of direct radical C Ar − H (hetero)aromatic functionalization involving fluorinated radicals. A compilation Functional Group Transfer Reagents and their diverse activation mechanisms leading to release radicals are discussed. The substrate scope for each is analyzed classified into three categories according electronic properties substrates. Density functional theory computational analysis provides insights chemical reactivity several through electrophilicity nucleophilicity parameters. Theoretical reduction potentials also highlights remarkable correlation between oxidizing ability. It established that highly (e.g. ⋅OCF 3 ) capable engaging single‐electron transfer (SET) processes rather than addition, which good agreement with experimental literature data. scale, based on barrier addition these benzene elaborated using high accuracy DLPNO‐(U)CCSD(T) method.

Language: Английский

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Transition-Metal and Solvent-Free Oxidative C–H Fluoroalkoxylation of Quinoxalinones with Fluoroalkyl Alcohols

Organic Letters, Journal Year: 2019, Volume and Issue: 21(12), P. 4698 - 4702

Published: June 6, 2019

The first example of oxidative C–H fluoroalkoxylation quinoxalinones with fluoroalkyl alcohols under transition-metal and solvent-free conditions is described. This approach provides the synthesis fluoroalkoxylated quinoxaline derivatives good to excellent yields mild reactions conditions. method can also be extended facile efficient histamine-4 receptor.

Language: Английский

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Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions

Green Chemistry, Journal Year: 2020, Volume and Issue: 23(1), P. 374 - 378

Published: Oct. 23, 2020

Aryl radicals were generated for the first time from aryl acyl peroxides in ethyl acetate under ambient conditions and visible-light illumination absence of any additive, metal catalyst, or external photosensitizer.

Language: Английский

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Promising reagents for difluoroalkylation

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(17), P. 2538 - 2575

Published: Jan. 1, 2020

This review describes recent advances in difluoroalkylation reactions using different substrates.

Language: Английский

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Visible-light-promoted acridine red catalyzed aerobic oxidative decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(3), P. 492 - 498

Published: Jan. 1, 2020

Visible-light-mediated procedure has been developed for the synthesis of 3-acyl quinoxalin-2(1H)-ones through acridine red catalyzed decarboxylative acylation α-oxo-carboxylic acids with quinoxalin-2(1H)-ones.

Language: Английский

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Direct C–H sulfenylation of quinoxalinones with thiols under visible-light-induced photocatalyst-free conditions

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(23), P. 6241 - 6245

Published: Jan. 1, 2019

We have developed a metal-free and catalyst-free visible-light-promoted direct C–H sulfenylation of quinoxalin-2(1H)-ones with thiols for the synthesis diverse 3-sulfenylquinoxalin-2(1H)-ones.

Language: Английский

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Visible Light‐Induced Photocatalytic C−H Perfluoroalkylation of Quinoxalinones under Aerobic Oxidation Condition

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 361(23), P. 5490 - 5498

Published: Sept. 16, 2019

Abstract An efficient approach using a photocatalytic strategy for C−H perfluoroalkylation of quinoxalinones under aerobic oxidation condition has been developed. Such transformation employs readily available sodium perfluoroalkanesulfinates as reagents and demonstrates good functional group compatibility, affording corresponding products in moderate to yields. Compared with previous procedures, this protocol uses oxygen oxidant, avoids the use external additive. A radical mechanism is involved reaction. magnified image

Language: Английский

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