Organophotoredox‐Catalyzed Late‐Stage Functionalization of Heterocycles

Hota, Sudhir Kumar; Jinan, Dilsha; Panda, Satya Prakash; Pan, Rittwika; Sahoo, Basudev; Murarka, Sandip

doi:10.1002/ajoc.202100234

Cited by 48 publications

(14 citation statements)

References 86 publications

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“…Although there are several reports on transition metal catalyzed multicomponent photoredox transformations, they suffer from limitations such as high cost, low sustainability and high toxicity. Organo-photoredox catalysis [54][55][56][57][58] is considered as a cost effective and sustainable alternative to transition metal based photocatalysis. It is based on the ability of certain organic dyes and molecules to undergo SET with organic substrates to generate reactive radical intermediates upon visible light irradiation.…”

Section: Organo Photoredox Catalysismentioning

confidence: 99%

Photoredox‐mediated Multicomponent Reactions

et al. 2022

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Multicomponent reactions (MCR's) provide a unique opportunity for synthetic chemists to achieve the synthesis of complex organic molecules in a single step. Although MCR are known for more than a century, their utility, in general, is limited to a narrow set of reactions due to the inherent difficulties in controlling the desired reactivity & selectivity with three or more components. Photoredox catalysis on the other hand has recently gathered more attention from synthetic chemists due to its simplicity and the new type of reactivity it can offer. In this direction, many new multicomponent reactions mediated by photoredox catalysis are reported. Given the importance of thsis special type of reaction and in order to further design new photomediated multicomponent reactions, a review of the existing reports is very essential. We have broadly divided this review based on the type of photocatalyst used for the multicomponent reaction such as metal photocatalysis, organophotoredox catalysis & dual transition metal-photoredox catalysis.

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Section: Organo Photoredox Catalysismentioning

confidence: 99%

Photoredox‐mediated Multicomponent Reactions

et al. 2022

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“…The subclass of such reactions in which a catalyst is activated by light (photoredox catalysis, Scheme 1, type IV), especially visible, has gained much attention in the last decade. A considerable number of good reviews was published, both general [19][20][21][22][23][24][25][26][27][28][29] and specialized on the specific types of organophotoredox catalysts, such as quinone derivatives [30,31], carbon nitrides [32,33], eosin [34][35][36], 4CzIPN [37,38], Bodipy derivatives [39], methylene blue [40], pyrylium salts [41], and perylene diimides [42]. Photochemical processes involving enantioselective organocatalysis were also reviewed [28].…”

Section: Introductionmentioning

confidence: 99%

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

Lopat’eva¹,

Krylov²,

Lapshin³

et al. 2022

Beilstein J. Org. Chem.

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Organocatalysis is widely recognized as a key synthetic methodology in organic chemistry. It allows chemists to avoid the use of precious and (or) toxic metals by taking advantage of the catalytic activity of small and synthetically available molecules. Today, the term organocatalysis is mainly associated with redox-neutral asymmetric catalysis of C–C bond-forming processes, such as aldol reactions, Michael reactions, cycloaddition reactions, etc. Organophotoredox catalysis has emerged recently as another important catalysis type which has gained much attention and has been quite well-reviewed. At the same time, there are a significant number of other processes, especially oxidative, catalyzed by redox-active organic molecules in the ground state (without light excitation). Unfortunately, many of such processes are not associated in the literature with the organocatalysis field and thus many achievements are not fully consolidated and systematized. The present article is aimed at overviewing the current state-of-art and perspectives of oxidative organocatalysis by redox-active molecules with the emphasis on challenging chemo-, regio- and stereoselective CH-functionalization processes. The catalytic systems based on N-oxyl radicals, amines, thiols, oxaziridines, ketone/peroxide, quinones, and iodine(I/III) compounds are the most developed catalyst types which are covered here.

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“…In this regard, visible light photoredox catalysis has emerged as an efficient and environmentally benign synthetic tool in fostering modern organic synthesis . The last decade has witnessed an upsurge in the application of visible light photoinduced synthetic transformations due to their mildness, sustainability, operational simplicity, and appreciable functional group tolerance.…”

Section: Introductionmentioning

confidence: 99%

Visible Light Photoredox-Catalyzed Direct C–H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts

2022

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A photoredox-catalyzed direct arylation of quinoxalin-2-(1H)-ones using diaryliodonium triflates as the convenient, stable, and cheap aryl source is described. A broad variety of quinoxalin-2-(1H)-ones are shown to react with structurally and electronically diverse diaryliodonium triflates, allowing efficient access to a wide variety of pharmaceutically important 3-arylquinoxalin-2-(1H)-ones. The presented method is attractive with regard to operational simplicity, mild conditions, broad scope, scalability, and high functional group tolerance.

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Organophotoredox‐Catalyzed Late‐Stage Functionalization of Heterocycles

Cited by 48 publications

References 86 publications

Photoredox‐mediated Multicomponent Reactions

Photoredox‐mediated Multicomponent Reactions

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

Visible Light Photoredox-Catalyzed Direct C–H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts

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