Heteroarene <i>N</i>‐Oxides as Oxygen Source in Organic Reactions

Petrosyan, A.M.; Hauptmann, Richy; Pospech, Jola

doi:10.1002/ejoc.201800152

Cited by 41 publications

(17 citation statements)

References 114 publications

(81 reference statements)

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“…rectangular cross-section is 2.213 with the cationic and 1.810 with the anionic porphyrin. Notably, the volume of the solution in the batch reactor is 50 cm 3 , while in the microreactor it is only 4.15 µL. This three orders of magnitude difference compensates the strongly deviating geometrical factors and optical pathlengths.…”

Section: Calculationsmentioning

confidence: 97%

“…Additionally, very promising results are obtained by reactions in which porphyrin complexes coordinated with certain metals are used as catalysts; therefore, scientists have studied a whole range of metals within porphyrin structures as well as their advantages in various catalytic oxidations [2]. There are examples of porphyrin complexes coordinated with ruthenium [3]. Manganese porphyrins have already been used in the past for various organic reactions.…”

Section: Introductionmentioning

confidence: 99%

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Photocatalytic Oxygenation of Heterostilbenes—Batch versus Microflow Reactor

et al. 2021

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On the basis of earlier results with furan and thiophene derivatives of benzobicyclo[3.2.1]octadiene, photocatalytic oxygenation of novel furo- and thieno heterostilbenes with water-soluble manganese(III) porphyrins offered suitable possibilities to study their reactivities and reaction pathways depending on the heteroatom and the catalyst charge. The experiments were carried out in two reactors types (batch and microflow) to investigate the geometric effects. NMR spectroscopy, GC, and UPLC/MS analyses were applied for identification and quantification of the products. As our results indicated, the 2-thienyl and the common p-tolyl groups in the starting compounds remained intact due to their stronger aromaticity. Hence, the thieno derivative underwent oxygenation only at the open-chain part of the molecule, and the rates of its reactions were much lower than those of the furyl analogue. The less stable furan ring was easily oxygenated, its products with highest ratios were 2-furanon derivatives. Epoxide formation occurred at the open-chain parts of both substrates preferably by the anionic catalyst. Nevertheless, the conversion rates of the substrates were higher with the cationic porphyrin, according to electrophilic attacks by photogenerated Mn(V)=O species. Additionally, the reactions were significantly faster in microflow reactors due to the more favorable circumstances of mass transfer, diffusion, and light penetration.

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Section: Calculationsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Photocatalytic Oxygenation of Heterostilbenes—Batch versus Microflow Reactor

et al. 2021

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“…[92][93][94][95] There are two features: the oxygen atom nucleophilicity in N-oxides and a high affinity of silicon to oxygen which aim at representing perfect properties in order to develop a synthetic methodology based on nucleophilic activation of organosilicon reagents. [96][97][98][99] Due to the N-O bond polarization, one can classify the heteroaromatic N-oxides properties as strong Lewis bases. [100][101][102][103] In this regard, those Lewis base catalysts which possess the pyridine oxide moiety-positioned in a chiral environment-have constituted a specific type of active catalysts.…”

Section: N-oxides Catalyzed the Silylation Of Hydroxyl Groupsmentioning

confidence: 99%

Recent advances in catalytic silylation of hydroxyl‐bearing compounds: A green technique for protection of alcohols using Si–O bond formations

Ashraf

Liu

et al. 2020

Applied Organom Chemis

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The development of catalytic silylation of alcohols under ambient reaction conditions plays an important role in organic synthesis. New silyl groups and methods for their introduction and removal are constantly being developed and offer chemists a wider range of options. In recent years, silyl protecting groups have been given expanded roles beyond their traditional use of temporarily rendering inactive alcohols. As silyl ether can be further converted to the parent alcohols in acidic conditions, silylation of alcohols can be regarded as an alternative method for hydroxyl protection under ambient reaction conditions. Merging the silyl protection/deprotection of alcohols with such modern methodologies, as green chemistry and nanoscience, has added additional value to these temporary components of synthetic intermediates. This review describes the historical background of the trimethylsilyl ethers preparation from alcohols using catalytic complexes and also the transformation of trimethylsilyl ethers into alcohol-containing compounds via deprecation techniques.

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“…The oxygenation of organic molecules plays a significant role in organic transformations . There are few reports in the literature that deal with an oxidative dinitrogen extrusion event where diazo compounds act as an oxygen acceptor in the oxygen-transfer process (Scheme a).…”

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confidence: 99%

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

2021

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A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

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Heteroarene N‐Oxides as Oxygen Source in Organic Reactions

Cited by 41 publications

References 114 publications

Photocatalytic Oxygenation of Heterostilbenes—Batch versus Microflow Reactor

Photocatalytic Oxygenation of Heterostilbenes—Batch versus Microflow Reactor

Recent advances in catalytic silylation of hydroxyl‐bearing compounds: A green technique for protection of alcohols using Si–O bond formations

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

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