Photo-Organocatalysis, Photo-Redox, and Electro- Organocatalysis Processes

“…(S)-2-((R)-hydroxy(2-nitrophenyl)methyl)cyclohexanone (3) [34]: 78 mg, yield: 63%. 1 H NMR (400.13 MHz, CDCl3) δ 8.14 (dd, 3 JH3′-H4′ = 8 Hz, 4 J H3′-H5′ = 11 Hz, 1H, H3′), 7.96 (dd, 3 JH6′-H5′ = 8 Hz, 4 J H6′-H4′ = 11 Hz, 1H, H6′), 7.79 (m, 2H, H5′,H4′), 5.43 (d, 3 JH*-H2 = 8 Hz, 1H, H * ), 3.47 (t, 3 JH2-H*, H3 = 8 Hz, 1H, H2), 2.43-2.34 (m, 2H, H6), 2.20-2.08 (m, 1H, H3), 1.70-1.51 (m, 4H, H4, H5), 1.25-1.13 (m, 1H, H3). 13…”

Section: Supplementary Materialsmentioning

confidence: 99%

“…The major challenge in asymmetric synthesis is the pursuit of novel "green" catalysts exhibiting both high activity and selectivity [1][2][3]. Frequently described as the "third pillar of asymmetric catalysis", organocatalysis indicates to synthetic chemists an alternative approach towards chiral molecules that does not depend on enzymes nor on transition metals.…”

Section: Introductionmentioning

confidence: 99%

“…(1)[32]: 93 mg, yield: 89% 1. H NMR (400.13 MHz, CDCl 3 ) δ 7.95 (d,3 J H3 -H4 = 8 Hz, 1H, H 3 ), 7.90 (d,3 J H6 -H5 = 8 Hz, 1H, H 6 ), 7.65 (t, 3 J H5 -H6 , H4 = 8 Hz, 1H, H 5 ), 7.43 (t, 3 J H4 -H5 , H3 = 8 Hz, 1H, H 4 ), 5.68 (d, 3 J H4-H3 = 8 Hz, 1H, H 4 ), 3.13 (dd, 3 J H3-H3, H4 = 8 Hz, 1H, H 3 ), 2.79 (dd, 3 J H3-H3, H4 = 8 Hz, 1H, H 3 ), 2.23 (s, 3H, H 1 ) 13. C NMR (100.61 MHz, CDCl 3 ) δ 208.20 (C 2 ), 147.24 (C 6 ), 138.28 (C 5 ), 133.91 (C 2 ), 128.27 (C 3 ), 124.26 (C 4 ), 65.53 (C 4 ), 51.18 (C 3 ), 30.00 (C 1 ).…”

mentioning

confidence: 99%

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Chiral Ionic Liquids Based on l-Cysteine Derivatives for Asymmetric Aldol Reaction

Zalewska¹,

Zakrzewska²,

Branco³

2022

Catalysts

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Structure, and consequently properties, of ionic liquids can be easily tailored by changing cation/anion combinations and/or attaching functional groups. By grafting enantiopure moieties to the framework of ionic liquid it is possible to prepare bioinspired chiral molecules that can serve as a reaction medium, additive or even asymmetric catalyst. In this context, new chiral ionic liquids (CILs), based on biomolecules, such as aminoacids (L-cysteine derivatives), have been synthesised and tested in asymmetric aldol condensation of aldehydes and ketones. The best results were obtained for CILs composed of S-methyl-L-cysteine cation and bis(trifluoromethane)sulfonimide anion, in the reaction of 2- or 4-nitrobenzaldehyde with acetone or cyclohexanone, giving the aldol product in moderate yields 70–76% and high ee values (up to 96%).

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“…Taking into account the good coverage of organophotoredox-catalysis in these reviews we decided to focus on another, less systematized subclass of processes catalyzed by redox-active molecules in the ground state (Scheme 1, type III). There are a number of reviews on specific groups of redox-organocatalyzed oxidative transformations [43][44][45][46][47][48][49][50][51][52][53][54][55][56] and organocatalyzed enantioselective radical reactions were recently discussed [57]. However, the field remains not overviewed in general and it is not consolidated as a research field.…”

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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Photo-Organocatalysis, Photo-Redox, and Electro- Organocatalysis Processes

Cited by 4 publications

References 70 publications

Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review

Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review

Chiral Ionic Liquids Based on l-Cysteine Derivatives for Asymmetric Aldol Reaction

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

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