Organic Reactions Promoted by Metal-Free Organic Dyes Under Visible Light Irradiation

Miyabe, Hideto

doi:10.5772/intechopen.70507

Cited by 8 publications

(10 citation statements)

References 57 publications

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“…Органічні барвники є більш екологічними та дешевшими. Індукторами фоторедокскаталізу апробовано еозин Y та еозин B, флуоресцеїн, метиленовий синій, бенгальська роза; розроблено чимало фотокаталізаторів на основі хіноліну та акридину [37].…”

Section: використання видимого світла як каталізатора реакційunclassified

“…Дією видимого світла проведено генерування арильних радикалів із діазонієвих солей. Фотохімічним ініціюванням за наявності еозину отримано продукти арилювання солями арендіазонію ароматичних гетероциклів [37][38][39][40]. Еозин ЕY як каталізатор одноелектронного переносу застосовано й у фотоініційованій реакції солей арендіазонію з алкінами [42].…”

Section: використання видимого світла як каталізатора реакційunclassified

“…Отож загальний цикл фотокаталізованих реакцій ініціюється випромінюванням видимим світлом: з основного стану отримують високоенергетичний збуджений стан барвника (схема 12) [37]. Далі фотокаталіз видимим світлом, залежно від умов реакції і природи барвника, може реалізовуватися двома шляхами перетворень барвника у збудженому стані Dye* [37].…”

Section: використання видимого світла як каталізатора реакційunclassified

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Metal-free catalysed reactions of unsaturated compounds with arenediazonium salts

Bilaya¹,

Rohovyk²

2020

Visnyk Lviv Univ. Ser. Chem.

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reactions are considered. It has been shown that nucleophiles, in particular acetate, trifluoroacetate, salicylate and galate ions, can catalyze the arylation reaction from the formation of intermediate diazoesters. Examples of metal-free photoinitiated reactions of arenediazonium salts and unsaturated compounds are given. The potential possibilities of using photocatalysis caused by visible light are considered. Photocatalysts that are directly involved in the transmission of light quantum are often the molecules of dyeseosin, fluorescein. It has been shown that photoinitiation can be successfully used for both arylation and anionylation reactions. Examples of nonmetallocatalyzed reactions through the formation of diazonium salts in situ are presented. It is stated that metal-free initiation can also be successfully used for carrying out intramolecular cyclization under reaction conditions. Therefore, the use of systems that are prone to single electron transfer (SET) can be successfully tested as a metalfree initiation of reactions of arenediazonium salts with alkenes.

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Section: використання видимого світла як каталізатора реакційunclassified

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Metal-free catalysed reactions of unsaturated compounds with arenediazonium salts

Bilaya¹,

Rohovyk²

2020

Visnyk Lviv Univ. Ser. Chem.

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“…The triplet 3 MB +* is a significantly more stable excited state 5 , with a triplet lifespan of τ f ~ 32 μs 5 , 6 . (More content and discussions about photoredox cycle catalyzed by dye 7 have been added to the supporting information file).…”

Section: Introductionmentioning

confidence: 99%

The development of Friedländer heteroannulation through a single electron transfer and energy transfer pathway using methylene blue (MB+)

Mohamadpour

2022

Sci Rep

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The radical Friedländer hetero-annulation of 2-aminoaryl ketone and -methylene carbonyl compound was used to develop a green tandem approach for the metal-free synthesis of polysubstitutedquinolines. At room temperature in an ethanol solvent, photo-excited state functions generated from MB+ were used as single-electron transfer (SET) and energy transfer (EnT) catalysts, utilizing visible light as a renewable energy source in the air atmosphere. The purpose of this research is to increase the use of a nonmetal cationic dye that is both inexpensive and widely available. High yields, energy-effectiveness, high atom economy, time-saving features of the reaction, and operational simplicity, and the least amount of a catalyst are the benefits of this study. As a result, a wide range of ecological and long-term chemical properties are obtained. Polysubstitutedquinolines' turnover number (TON) and turnover frequency (TOF) have been calculated. Surprisingly, such cyclization can be accomplished on a gram scale, indicating that the process has industrial potential.

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“…Утворення йон-радикалів постулюють автори [16] і для карбонілювання солей арендіазонію, каталізованого флуоресцеїном: Одним із перспективних нейтральних нуклеофілів для мультикомпонентних реакцій є оксид азоту(II). Однак дослідники не раз наголошували на порівняно низькій реакційній здатності оксиду азоту стосовно вуглець-центрованих радикалів.…”

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Three-Component Reactions of Unsaturated Compounds With Arenediasonium Salts and Neutral Nucleophils. Arylsulfonylation

Bila¹,

SOLTYS²,

Обушак³

2020

Proc. Shevchenko Sci. Soc. Chem. Sci.

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The results of recent achievements on the interaction of arenediazonium salts with unsaturated compounds in the presence of neutral nucleophiles are summarized. New examples of multicomponent transformations with the participation of such neutral nucleophiles as CO (arylcarbonylation), NO (arylnitrosylation), aceto¬nitrile (aminoarylation), SO2 (arylsulfonylation) and others are given. These reactions can be applied to alkenes, alkynes, aromatic compounds. Mild reaction conditions allow the use of reagents with different functional groups. Reactions of this type open up the possibility of one-step production of complex poly¬functional compounds. Catalytic systems are quite diverse for these transformations: it is catalysis involving transition metals, platinum group metals. Prospects for the use of arenediazonium salts in multicomponent transfor¬ma-tions according to the concepts of «green» chemistry are outlined – it is photoinitiation by visible and ultraviolet radiation, acid-base catalysis. The role of catalysis in the process, the role of complex intermediates and reaction mechanisms are analyzed. For most processes, the SET reaction mechanism is implemented through the formation of an alkene intermediate ion radical, the stability of which depends on the nature of the substituent near the double bond. Particular attention is paid to arylsulfonylation reactions, because the arylsulfonyl group is one of the many important biologically active molecules. Arylsulfonylation reactions of alkenes with the participation of transition metals or under conditions of metal-free catalysis are considered. Examples of arylsulfonylation of the C=C bond using sulfinic acids, their salts and hydrazides are given. An available method for producing functionalized sulfones is the multicomponent interaction of arenediazonium salts, alkenes and SO2. The arylsulfonylation reaction occurs as a series of successive reactions involving the generation of a catalyst, the decomposition of arenediazonium cations, the addition of an aryl group, a nucleophile to a multiple bond, and the formation of the final products. The use of functionalized alkenes allows to obtain functionalized arylsulfones in one step. This functionalization expands the scope of use of arylsulfones, in particular, for studies of biological activity. The progress made in the development of effective strategies for the production of arylsulfones opens new opportunities for further research.

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Organic Reactions Promoted by Metal-Free Organic Dyes Under Visible Light Irradiation

Cited by 8 publications

References 57 publications

Metal-free catalysed reactions of unsaturated compounds with arenediazonium salts

Metal-free catalysed reactions of unsaturated compounds with arenediazonium salts

The development of Friedländer heteroannulation through a single electron transfer and energy transfer pathway using methylene blue (MB+)

Three-Component Reactions of Unsaturated Compounds With Arenediasonium Salts and Neutral Nucleophils. Arylsulfonylation

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