Relevant bibliographies by topics / Photoredox catalytic system

Academic literature on the topic 'Photoredox catalytic system'

Author: Grafiati
Published: 25 May 2024

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Contents

  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Journal articles on the topic "Photoredox catalytic system":

1

Yang, Qiong, Fengqian Zhao, Na Zhang, Mingke Liu, Huanhuan Hu, Jingjie Zhang, and Shaolin Zhou. "Mild dynamic kinetic resolution of amines by coupled visible-light photoredox and enzyme catalysis." Chemical Communications 54, no. 100 (2018): 14065–68. http://dx.doi.org/10.1039/c8cc07990k.

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A mild and efficient dynamic kinetic resolution (DKR) of amines was achieved by combining visible-light-induced photoredox catalysis and enzyme catalysis. This dual catalytic system was appropriate for both monoamines and 1,4-diamines.
2

Leadbeater, Nicholas, Jyoti Nandi, and Mason Witko. "Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles." Synlett 29, no. 16 (September 12, 2018): 2185–90. http://dx.doi.org/10.1055/s-0037-1610272.

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A method to oxidize aromatic aldehydes to nitriles has been developed. It involves a dual catalytic system of 4-acetamido-TEMPO and visible-light photoredox catalysis. The reaction is performed using ammonium persulfate as both the terminal oxidant and nitrogen source.
3

Tlahuext-Aca, Adrian, Matthew N. Hopkinson, Basudev Sahoo, and Frank Glorius. "Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts." Chemical Science 7, no. 1 (2016): 89–93. http://dx.doi.org/10.1039/c5sc02583d.

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Hu, Xia, Guoting Zhang, Faxiang Bu, Xu Luo, Kebing Yi, Heng Zhang, and Aiwen Lei. "Photoinduced oxidative activation of electron-rich arenes: alkenylation with H2 evolution under external oxidant-free conditions." Chemical Science 9, no. 6 (2018): 1521–26. http://dx.doi.org/10.1039/c7sc04634k.

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Hossain, Asik, Aditya Bhattacharyya, and Oliver Reiser. "Copper’s rapid ascent in visible-light photoredox catalysis." Science 364, no. 6439 (May 2, 2019): eaav9713. http://dx.doi.org/10.1126/science.aav9713.

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Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of photoredox processes capitalizes on precious metal ruthenium(II) or iridium(III) complexes that serve as single-electron reductants or oxidants in their photoexcited states. As a low-cost alternative, organic dyes are also frequently used but in general suffer from lower photostability. Copper-based photocatalysts are rapidly emerging, offering not only economic and ecological advantages but also otherwise inaccessible inner-sphere mechanisms, which have been successfully applied to challenging transformations. Moreover, the combination of conventional photocatalysts with copper(I) or copper(II) salts has emerged as an efficient dual catalytic system for cross-coupling reactions.
6

Naumann, Robert, Christoph Kerzig, and Martin Goez. "Laboratory-scale photoredox catalysis using hydrated electrons sustainably generated with a single green laser." Chem. Sci. 8, no. 11 (2017): 7510–20. http://dx.doi.org/10.1039/c7sc03514d.

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A combined photokinetical approach helped develop and optimize a green-light driven photoredox catalytic system that generates a “super-reductant” with simple instrumentation, consumes only a bioavailable donor, and provides very high turnover numbers.
7

Pagire, Santosh K., Naoya Kumagai, and Masakatsu Shibasaki. "Introduction of a 7-aza-6-MeO-indoline auxiliary in Lewis-acid/photoredox cooperative catalysis: highly enantioselective aminomethylation of α,β-unsaturated amides." Chemical Science 11, no. 20 (2020): 5168–74. http://dx.doi.org/10.1039/d0sc01890b.

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An efficient cooperative chiral Lewis acid and photoredox catalytic system towards the highly enantioselective radical conjugate addition of α-amino radicals to α,β-unsaturated amides is developed with the implementation of unique auxiliaries.
8

Kostromitin, Vladislav S., Vitalij V. Levin, and Alexander D. Dilman. "Atom Transfer Radical Addition via Dual Photoredox/Manganese Catalytic System." Catalysts 13, no. 7 (July 19, 2023): 1126. http://dx.doi.org/10.3390/catal13071126.

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Atom transfer radical addition of bromonitromethane and 1,2-dibromotetrafluoroethane to alkenes is described. The reaction is performed under blue light irradiation using two catalysts: 4CzIPN and manganese (II) bromide. The cyanoarene photocatalyst serves for the redox activation of starting organic bromide, while the manganese salt facilitates the trapping of the alkyl radical with the formation of the carbon–bromine bond.
9

Li, Heng-Hui, Shaoyu Li, Jun Kee Cheng, Shao-Hua Xiang, and Bin Tan. "Direct arylation of N-heterocycles enabled by photoredox catalysis." Chemical Communications 58, no. 27 (2022): 4392–95. http://dx.doi.org/10.1039/d2cc01212j.

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A photoredox catalytic system was developed to construct N-heterobiaryls via direct arylation from readily accessible substrates. While phenols act as both coupling partner and proton donor, regular arenes were also applicable with HFIP as a solvent.
10

Mitsunuma, Harunobu, Hiromu Fuse, Yu Irie, Masaaki Fuki, Yasuhiro Kobori, Kosaku Kato, Akira Yamakata, Masahiro Higashi, and Motomu Kanai. "(Invited) Identification of a Self-Photosensitizing Hydrogen Atom Transfer Organocatalyst System." ECS Meeting Abstracts MA2023-01, no. 14 (August 28, 2023): 1355. http://dx.doi.org/10.1149/ma2023-01141355mtgabs.

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The carbon-hydrogen (C-H) bond is a fundamental chemical bond that constitutes organic molecules, and its direct conversion leads to highly efficient molecular synthesis. In recent years, the hydrogen atom transfer (HAT) catalysis using the energy of visible light, has been attracting attention. However, existing methods require the use of photoredox catalysts such as organic molecules with complex structures and expensive metal complexes. In this study, we developed an organocatalytic system that mimics the electron transfer process of enzymes in vivo and promotes functionalization of stable C-H bond without photoredox catalyst. We designed a thiophosphoric acid catalyst that contains both a redox-active binaphthyl moiety and a sulfur atom. We found that this catalyst forms charge-transfer complexes with electron-deficient heteroaromatics and catalytically produces thyil radical via multi-step electron transfer under visible light irradiation. Based on the above design, we decided to investigate the formation of active HAT catalytic species in the absence of photoredox catalysis by the Minisci-type reaction using aldehydes and N-heteroaromatic rings. The results of the study confirmed that 29% of the product was obtained when using binaphtyl thiophosphoric acid (TPA) catalyst, as expected. Yield improved to 80% when an electron-donating group was introduced to the binaphthyl skeleton to enhance the donor-acceptor interaction. Changing the binaphthyl skeleton and thiophosphoric acid moieties markedly reduced reactivity, indicating that the presence of a sulfur atom in addition to a rigid binaphthyl skeleton is essential for the efficient reaction progress. With this optimized condition, alkylation of N-heteroaromatic rings by C-H bond activation of alcohols was found to proceed. Dehydrogenation of alcohols and benzylation of imines were also successfully achieved by using N-heteroaromatic catalyst. The mechanism of the electron transfer process has been confirmed by spectroscopic and computational methods, and will be presented in detail in the lecture. Figure 1
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Journal articles

Dissertations / Theses on the topic "Photoredox catalytic system":

1

Fall, Arona. "Donneurs d’électrons organiques : développement d’un nouveau système catalytique photoredox." Electronic Thesis or Diss., Aix-Marseille, 2021. http://www.theses.fr/2021AIXM0607.

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Durant ces dernières décennies, la réactivité des donneurs d’électrons organiques de type énamine (DEO) a été largement exploitée dans des réactions de réduction par transfert électronique. De part leurs forts pouvoir réducteur avec des potentiels redox exceptionellement négatifs, les DEOs sont capables de transférer spontanément un ou deux électrons à des substrats organiques, formant ainsi des intermédiaires radicalaires ou anioniques. Cependant, ces DEOs sont toujours utilisés en quantité stœchiométrique, ce qui limite leur compétivité face aux catalyseurs organométalliques et organiques.Les travaux de cette thèse consistent à répondre à cette problématique en développant un nouveau système catalytique avec ces DEOs. Pour cela, plusieurs stratégies ont été envisagées. Dans une première méthode, une quantité catalytique du DEO serait utilisée pour amorcer le transfert d’électron pour la réduction du substrat. L’oxydation d’intermédiaires radicalaires générés, permettrait alors de régénérer le DEO. Cette stratégie n’a malheureusement pas donné de résultat. Une seconde méthode consisterait à régénérer le DEO à partir de la forme oxydée DEO2+, stable à l’air et d’un donneur d’électron sacrificiel (amine tertiaire, dithionite de sodium ou Rongalite®) sous photoactivation. Plusieurs étapes d’optimisation ont permis d’aboutir à un système catalytique photoredox efficace avec la forme oxydée comme photocatalyseur et la Rongalite® en tant que donneur sacrificiel. Ce nouveau système catalytique photoredox a été appliqué à la réduction de divers groupements fonctionnels (sulfone, halogénure d’aryle, triflate) par transfert mono et biélectronique
During this last decade, the reactivity of enamine-based organic electron donor (OED) has been widely explored in electron transfer processes. With exceptionally negative redox potentials, OEDs spontaneously promote single (SET) or double electron transfer (DET) to an organic substrate, to form radical or anionic intermediates. However, the use of stoichiometric amount of OEDs limits their competitivity compared to their organometallic and organic catalysts. This thesis project consisted in developing a new catalytic system with OEDs. Different strategies were envisaged. In a first method a catalytic amount of OED would initiate the electron transfer to reduce the substrate. The oxidation of the generated radical intermediate would allow the regeneration of OED. Unfortunately, this strategy was unsuccessful. The second strategy would consist in regenerating the OED from its air-stable oxidized form OED2+ and a sacrificial electron donor (tertiary amine, sodium dithionite or Rongalite®) under photoactivation. Several optimizing steps allowed the development of a new efficient catalytic photoredox system with the oxidized form as photocatalyst and Rongalite® as sacrificial electron donor. This new photoredox catalytic system was applied to the reduction of various functionals groups (sulfone, aryl halide and triflate) by single electron transfer (SET) and double electron transfer (DET). The reactivity of the photocatalytic system was also explored in radical addition reactions

Book chapters on the topic "Photoredox catalytic system":

1

Hill, C. L., and C. M. Prosser-McCartha. "Photocatalytic and Photoredox Properties of Polyoxometalate Systems." In Catalysis by Metal Complexes, 307–30. Dordrecht: Springer Netherlands, 1993. http://dx.doi.org/10.1007/978-94-017-2626-9_10.

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2

Subramaniann, H., and M. P. Sibi. "2.12 Asymmetric Catalysis of Radical Reactions." In Free Radicals: Fundamentals and Applications in Organic Synthesis 2. Stuttgart: Georg Thieme Verlag KG, 2021. http://dx.doi.org/10.1055/sos-sd-233-00202.

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AbstractSynthetic methodologies based on radical chemistry are efficient and powerful tools for the construction of carbon–carbon and carbon–heteroatom bonds. This chapter highlights the significance of asymmetric catalysis in free-radical reactions. Several asymmetric catalytic principles, ranging from early chiral Lewis acid and organocatalytic activation to recent photoredox and transition-metal-based asymmetric catalytic systems, are discussed.
3

Hutskalova, V., and C. Sparr. "15.9.4 Synthesis and Applications of Acridinium Salts (Update 2022)." In Knowledge Updates 2022/1. Stuttgart: Georg Thieme Verlag KG, 2022. http://dx.doi.org/10.1055/sos-sd-115-00850.

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AbstractThis chapter is an update to the earlier Science of Synthesis contribution (Section 15.9.3), covering selected methods for the preparation and the diverse fields of application of acridinium salts. The most important classical and recently published routes toward acridinium core construction are described and categorized according to key retrosynthetic disconnections. The utility of acridinium moieties in supramolecular chemistry is showcased by examples for various supramolecular switches containing this heterocyclic system. The application of acridinium salt derivatives as chemosensors for the detection of anionic species is also shown. Furthermore, the chapter features recent representative methods within the field of photoredox catalysis using acridinium salts as photocatalysts.
4

Lambert, Tristan H. "Reactions of Alkenes." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0031.

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Paul J. Chirik at Princeton University reported (Science 2012, 335, 567) an iron catalyst that hydrosilylates alkenes with anti-Markovnikov selectivity, as in the conversion of 1 to 2. A regioselective hydrocarbamoylation of terminal alkenes was developed (Chem. Lett. 2012, 41, 298) by Yoshiaki Nakao at Kyoto University and Tamejiro Hiyama at Chuo University, which allowed for the chemoselective conversion of diene 3 to amide 4. Gojko Lalic at the University of Washington reported (J. Am. Chem. Soc. 2012, 134, 6571) the conversion of terminal alkenes to tertiary amines, such as 5 to 6, with anti-Markovnikov selectivity by a sequence of hydroboration and copper-catalyzed amination. Related products such as 8 were prepared (Org. Lett. 2012, 14, 102) by Wenjun Wu at Northwest A&F University and Xumu Zhang at Rutgers via an isomerization-hydroaminomethylation of internal olefin 7. Seunghoon Shin at Hanyang University (experimental work) and Zhi-Xiang Yu at Peking University (computational work) reported (J. Am. Chem. Soc. 2012, 134, 208) that 9 could be directly converted to bicyclic lactone 11 with propiolic acid 10 using gold catalysis. A nickel/Lewis acid multicatalytic system was found (Angew. Chem. Int. Ed. 2012, 51, 5679) by the team of Professors Nakao and Hiyama to effect the addition of pyridones to alkenes, such as in the conversion of 12 to 13. Radical-based functionalization of alkenes using photoredox catalysis was developed (J. Am. Chem. Soc. 2012, 134, 8875) by Corey R.J. Stephenson at Boston University, an example of which was the addition of bromodiethyl malonate across alkene 14 to furnish 15. Samir Z. Zard at Ecole Polytechnique reported (Org. Lett. 2012, 14, 1020) that the reaction of xanthate 17 with terminal alkene 16 led to the product 18. The radical-based addition of nucleophiles including azide to alkenes with Markovnikov selectivity (cf. 19 to 20) was reported (Org. Lett. 2012, 14, 1428) by Dale L. Boger at Scripps La Jolla using an Fe(III)/NaBH4-based system. A remarkably efficient and selective catalyst 22 was found (J. Am. Chem. Soc. 2012, 134, 10357) by Douglas B. Grotjahn at San Diego State University for the single position isomerization of alkenes, which effected the transformation of 21 to 23 in only half an hour.

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