Recent Progress on Photocatalytic Synthesis of Ester Derivatives and Reaction Mechanisms

Deng, Yiqiang; Yang, Tianbao; Wang, Hui; Yang, Chong; Cheng, Lihua; Yin, Shuang‐Feng; Kambe, Nobuaki; Qiu, Renhua

doi:10.1007/s41061-021-00355-5

Cited by 11 publications

(6 citation statements)

References 103 publications

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“…To date, only a handful of examples of photo-generated 1,3-dicarbonyl radicals have been reported (Figure 1b). 41 For example, Fensterbank, Goddard, and Ollivier have reported the oxidative chemistry of aromatic β-ketoesters in radical allylations and oxidative dimerizations. 42 Wu and Xia have reported the use of 1,3-dicarbonyl radicals in cascade reactions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Photoredox catalysis presents an opportunity to drastically reduce the amount of transition metal used in this class of oxidation reactions. To date, only a handful of examples of photo-generated 1,3-dicarbonyl radicals have been reported (Figure b) . For example, Fensterbank, Goddard, and Ollivier have reported the oxidative chemistry of aromatic β-ketoesters in radical allylations and oxidative dimerizations .…”

Section: Introductionmentioning

confidence: 99%

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Photoredox-Catalyzed Oxidation of Anions for the Atom-Economical Hydro-, Amido-, and Dialkylation of Alkenes

et al. 2022

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Photoredox catalysis has become a powerful method to generate free radical intermediates in organic synthesis. This report describes the use of photoredox catalysis to directly oxidize common nucleophilic anions to access electrophilic 1,3-dicarbonyl and amidyl radical intermediates. First, conjugate bases of 1,3-dicarbonyls were oxidized to neutral radical species for intramolecular hydro-and dialkylation of alkenes. This overall redox-neutral process provided cyclopentanone products in excellent yields (up to 96%). The scope included a variety of styrene radical acceptors and products with newly formed vicinal quaternary carbons. This process was then extended to the synthesis of pyrrolidinones by alkene amidoalkylation that proceeded via N-aryl amidyl radical intermediates in good yield (up to 85%). These reactions were characterized by their mild conditions, high atom economy, and the absence of stoichiometric byproducts. Mechanistic and computational studies supported a stepwise proton-coupled electron transfer mechanism, where an "electron borrowing" photocatalyst oxidizes an anion and reduces a benzylic radical after bond formation.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoredox-Catalyzed Oxidation of Anions for the Atom-Economical Hydro-, Amido-, and Dialkylation of Alkenes

et al. 2022

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“…Additionally, some photosensitive proteins have photosensitive activity and may undergo oxidative damage under BL and degrade to small molecular components. Visible light can also directly break the bonds of compounds and cause photodegradation (Deng et al ., 2021). The catalytic effects of oxidation on different wavelengths of light have been shown to be: Blue > Green > Red > Yellow (Yang et al ., 2022).…”

Section: Discussionmentioning

confidence: 99%

Effect of different monochromatic lights on nutritional, antioxidant properties and spore microstructure of dried mushroom (Suillus granulatus)

Wang,

Feng,

et al. 2024

Int J of Food Sci Tech

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SummaryMonochromatic light has been shown to improve the flavour quality of dried mushrooms, but its effect on the nutritional, bioactive, antioxidant, rehydration and textural properties has not been studied. In this study, the effects of monochromatic light on these qualities of the dried Suillus granulatus were investigated and the porous characteristics and spore morphology were observed. The results showed that contents of soluble sugars, soluble proteins, flavonoid, phenolics, DPPH and rehydration under blue light were higher on the sixth day, it was 1.85 times, 1.58 times, 1.27 times and 1.20 times of the lowest content, respectively. While ABTS and FRAP were higher on the ninth day. The values are 33.5% and 0.749 mmol/LFeSO4, respectively. The texture of rehydrated mushrooms was higher under red light and lower under blue light. Clear pore structure and severely deformed spores can be observed under blue light, revealing the reason why mushrooms have better qualities under light. Correlation analysis results showed that nutrients, active components, antioxidant activity and rehydration showed a strong positive correlation. Totally, blue light is a promising processing technology to improve the quality of dried mushrooms.

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“…However, from an industrial point of view, we have also to consider the possible drawbacks and environmental impacts relate to such reaction. For instance, the use of hazardous chemicals and toxic solvents, the lack of substrate selectivity, excessive consumption of energy and possible corrosion of the equipment, which can influence the sustainability of the process [3,4,8,9,44]. Among these points, some attention should be paid to the addition of strong Brönsted acids, which could lead to corrosion problems in the reaction vessel and in the equipment, and to the addition of extra phosphine ligands, which could increase the toxic-related problems, e.g.…”

Section: Introductionmentioning

confidence: 99%

New Sustainable Pd(II)/Fe(III) Catalytic System Very Efficient in the Hydromethoxycarbonylation of 1-octene

Vavasori,

Fantinel,

Ronchin

et al. 2024

Period. Polytech. Chem. Eng.

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In order to increase the catalytic activity of the Pd(II)-complexes in the alcoxycarbonylation of 1-olefins, the presence in solution of a strong Brönsted acid together with a phosphine ligand is usually required. From an industrial point of view, such two additives, however, influenced the sustainability of the process mainly caused by the related corrosion of the reaction vessel and the toxicity of the phosphine ligand.In this paper, the methoxycarbonylation of 1-octene has been efficiently carried out by using the [Pd(TsO)2(PPh3)2]/FeCl3 catalyst system. The catalyst is very active also without addition of PPh3, reaching the TON of ca. 1300 (mol/mol) in 2 hours by using the Fe(III)/Pd(II) = 400/1 (mol/mol) system. Such value is higher than the values obtained by using the traditional strong Brönsted acid TsOH or other Lewis acid such as AlCl3, in the presence of PPh3. The reaction takes place with the formation of two isomeric products of linear and branched structures with a yield towards the linear isomer of ca. 80%.

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Recent Progress on Photocatalytic Synthesis of Ester Derivatives and Reaction Mechanisms

Cited by 11 publications

References 103 publications

Photoredox-Catalyzed Oxidation of Anions for the Atom-Economical Hydro-, Amido-, and Dialkylation of Alkenes

Photoredox-Catalyzed Oxidation of Anions for the Atom-Economical Hydro-, Amido-, and Dialkylation of Alkenes

Effect of different monochromatic lights on nutritional, antioxidant properties and spore microstructure of dried mushroom (Suillus granulatus)

New Sustainable Pd(II)/Fe(III) Catalytic System Very Efficient in the Hydromethoxycarbonylation of 1-octene

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