Direct Functionalization of para‐Quinones: A Historical Review and New Perspectives

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(27)

Опубликована: Май 21, 2024

Abstract The direct functionalization of quinones has always fascinated research communities due to their biological and redox activities subsequent application. Quinone motifs play a vital role as precursors for many bioactive compounds materials; hence, ingenious methodologies have been elaborated exploring these units. A significant part the synthetic strategies towards functionalized achieved by installing substituents on hydroquinones, phenols, or quinone itself different oxidative coupling reactions via radical pathways with without utilization metal catalysts. simple C−H bond remains challenging inherited electronic nature high dissociation energy. This review article summarizes recent advancement made through quinones. Our primary focus will be approaches mechanistic that appeared in last two decades, along short historical importance family.

Язык: Английский

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Synthesis of Acylhydroquinones through Visible-Light-Mediated Hydroacylation of Quinones with α-Keto Acids

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1669 - 1680

Опубликована: Янв. 11, 2024

A mild and eco-friendly visible-light-induced protocol for the hydroacylation of quinones with α-keto acids has been developed. In absence any catalyst or additive, decarboxylative proceeded smoothly under visible-light irradiation at room temperature. wide range were well-tolerated afforded products up to 88% isolated yield. The reaction can be scaled up, induced groups are useful further synthetic applications. Preliminarily, mechanistic studies indicated that photoactive absorb visible light facilitate transformation.

Язык: Английский

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Paired electrolysis enables weak Brønsted base-promoted amination of arenes with N,N-dialkyl formamides as the amine source

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(19), С. 5479 - 5487

Опубликована: Янв. 1, 2024

A paired electrolysis enabled amination of arenes using N , -dialkyl formamides as the amine source for synthesis arylamines without need chemical oxidants, metal catalysts or high temperatures is reported.

Язык: Английский

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Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

European Journal of Organic Chemistry, Год журнала: 2023, Номер unknown

Опубликована: Авг. 31, 2023

Abstract Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over past decades, a lot efforts have been put on development photocatalytic cascades employing both metal‐based purely organic catalysts. Despite effectiveness these protocols, catalyst‐ additive‐free light‐induced are gaining momentum thank their efficiency, operational simplicity sustainability. The increasing number papers published field in last years is proof appeal transformations. In Review, we discuss multicomponent mediated by light with focus photocatalyst‐ processes. most recent advances synthesis complex nitrogen‐, oxygen‐, sulphur‐ selenium‐heterocycles together analysed emphasis experimental mechanistic studies.

Язык: Английский

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Synthesis of 3,5-Disubstituted-1,2,4-thiadiazoles via NaH–DMF-Promoted Dehydrogenative Intramolecular N–S Bond Formation

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4453 - 4460

Опубликована: Март 26, 2024

A facile transition-metal-free synthesis of 3,5-bis(het)aryl/arylaminothiadiazoles has been reported. The overall protocol involves base-mediated tandem thioacylation amidines with dithioesters or aryl isothiocyanates in DMF solvent and subsequent situ intramolecular dehydrogenative N–S bond formation thioacylamidine intermediates under an inert atmosphere. probable mechanism involving a carbamoyl anion, generated by deprotonation DMF, acting as radical initiator suggested.

Язык: Английский

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Recent advances on naphthoquinone-imidazolyl and naphthoquinone-thiazolyl derivatives as photoinitiators of photopolymerization

European Polymer Journal, Год журнала: 2024, Номер 219, С. 113401 - 113401

Опубликована: Авг. 27, 2024

Язык: Английский

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TEMPO-Mediated Direct C(sp²)–H Alkoxylation/Aryloxylation of 1,4-Quinones

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 4, 2025

A convenient and efficient transition-metal-free method has been developed for the C(sp

Язык: Английский

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Oxidative Aminotrifluoromethylation of 1,4-Naphthoquinone

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13117 - 13127

Опубликована: Сен. 3, 2024

A strategy for convenient and precise oxidative aminotrifluoromethylation of 1,4-naphthoquinone with the Togni reagent amines has been demonstrated via a radical process. This method allows efficient access preparation wide range CF

Язык: Английский

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Visible Light Mediated Cyclization of Ynones for the Synthesis of 3‐Alkyl N‐Fused Indoles via Csp³−H Bond Functionalization

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4533 - 4537

Опубликована: Ноя. 14, 2023

Abstract A visible‐light induced approach has enabled the synthesis of 3‐alkyl indole from ynones via C sp 3 −H bond functionalization. This protocol proceeded under base‐free conditions andat room temperature, providing a series motifs in 39% to 90% yields (44 examples). Preliminary mechanistic studies suggest that radical process should be involved this transformation.

Язык: Английский

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Blue‐Light Irradiated Mn(0)‐Catalyzed Hydroxylation and C(sp³)−H Functionalization of Unactivated Alkanes with C(sp²)−H Bonds of Quinones for Alkylated Hydroxy Quinones and Parvaquone

Chemistry - A European Journal, Год журнала: 2023, Номер 30(12)

Опубликована: Ноя. 23, 2023

Abstract Site‐selective C( sp 3 )−H functionalization of unreactive hydrocarbons is always challenging due to its inherited chemical inertness, slightly different reactivity various C−H bonds, and intrinsically high bond dissociation energies. Here, a site‐selective alkylation naphthoquinone with unactivated using Mn 2 (CO) 10 as catalyst under blue‐light (457 nm) irradiation without any external acid or base pre‐functionalization presented. The selective tertiary over secondary primary bonds in abundant feedstocks was achieved, hydroxylation quinones realized situ by employing the developed methodology. This protocol provides new catalytic system for direct construction high‐value‐added compounds, namely, parvaquone (a commercially available drug used treat theileriosis ) derivatives ambient reaction conditions. Moreover, this operationally simple applies linear‐, branched‐, cyclo‐alkanes degrees site selectivity irradiated conditions could provide rapid straightforward access versatile methodologies upgrading feedstock chemicals. Mechanistic insight radical trapping, scavenging, EPR, other controlled experiments well corroborated DFT studies suggest that proceeds pathway.

Язык: Английский

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