Visible Light-Induced Aerobic Oxidative Dehydrogenation of C–N/C–O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments

Torregrosa-Chinillach, Alejandro; Chinchílla, Rafael

doi:10.3390/molecules27020497

Cited by 15 publications

(7 citation statements)

References 230 publications

(313 reference statements)

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“…Notably, few single-molecule photocatalysts 32 or extended porous organic polymers 33 have been used earlier for N-heterocycle dehydrogenation reactions. In the case of porous organic polymers, the photoactive motif was incorporated in the building block.…”

Section: Mechanistic Detailsmentioning

confidence: 99%

Photochemical oxidative dehydrogenation of saturated N-heterocycles by an iminoquinone

Mandal,

Bains,

Roy

et al. 2023

Catal. Sci. Technol.

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Section: Mechanistic Detailsmentioning

confidence: 99%

Photochemical oxidative dehydrogenation of saturated N-heterocycles by an iminoquinone

Mandal,

Bains,

Roy

et al. 2023

Catal. Sci. Technol.

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“…In terms of catalysis, the scope of application of IOSs is diverse, due to the wide variety of these solids. They can be found in many organocatalytic processes, being of particular importance as photocatalysts [ 14 , 15 ], or asymmetric phase-transfer catalysts [ 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Ionic Organic Solid 1,3-Bis(sulfomethyl)imidazoliumate as an Effective Metal-Free Catalyst for Sustainable Organic Syntheses

2023

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The 1,3-bis(sulfomethyl)imidazole (bsmim) was effectively prepared by a multicomponent reaction, employing aminomethanesulfonic acid, glyoxal, and formaldehyde. The catalytic activity of bsmim was tested in the synthesis of quinoline derivatives, by means of the Friedländer reaction, and in the allylic substitution of alcohols with nitrogen-containing heterocycles. The performance of sulfo-imidazole derivative (bsmim) resulted in higher comparison with the carboxyimidazole analogs (bcmim and bcmimCl), under the same reaction conditions. This type of ionic organic solid allows the promotion of reactions in the absence of solvent and mild reaction conditions, which improves the sustainability of organic synthetic processes.

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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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Visible Light-Induced Aerobic Oxidative Dehydrogenation of C–N/C–O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments

Cited by 15 publications

References 230 publications

Photochemical oxidative dehydrogenation of saturated N-heterocycles by an iminoquinone

Photochemical oxidative dehydrogenation of saturated N-heterocycles by an iminoquinone

Ionic Organic Solid 1,3-Bis(sulfomethyl)imidazoliumate as an Effective Metal-Free Catalyst for Sustainable Organic Syntheses

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

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