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Journal articles on the topic 'Metal-free oxidation'

Author: Grafiati

Published: 9 March 2023

Last updated: 31 July 2025

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1

Wang, Xi, and Yingwei Li. "Nanoporous carbons derived from MOFs as metal-free catalysts for selective aerobic oxidations." Journal of Materials Chemistry A 4, no. 14 (2016): 5247–57. http://dx.doi.org/10.1039/c6ta00324a.

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A new kind of metal-free catalyst comprised of highly graphitized N-doped nanoporous carbons from direct carbonization of metal–organic frameworks (MOFs) turns out to be an excellent metal-free catalyst for a series of liquid-phase oxidation reactions including aerobic oxidations of cyclohexane and toluene as well as oxidative coupling of amines.

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2

Zhao, Rong, Denghu Chang, and Lei Shi. "Recent Advances in Cyclic Diacyl Peroxides: Reactivity and Selectivity Enhancement Brought by the Cyclic Structure." Synthesis 49, no. 15 (2017): 3357–65. http://dx.doi.org/10.1055/s-0036-1588458.

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Preliminarily studies on cyclic diacyl peroxides have shown novel and superior reactivities compared with their acyclic diacyl peroxide counterparts in many reaction types. After summarizing the methods available for the preparation of cyclic diacyl peroxides and describing their structural features, this review brings together an overview of their reactivities with respect to oxidations and decarboxylations, and demonstrates the advantages of reactions with cyclic diacyl peroxides, which include metal-free, additive-free, milder conditions, higher yields and better selectivities.1 Introductio

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3

Uyanik, Muhammet, Dai Nagata, and Kazuaki Ishihara. "Hypoiodite-catalysed oxidative homocoupling of arenols and tandem oxidation/cross-coupling of hydroquinones with arenes." Chemical Communications 57, no. 88 (2021): 11625–28. http://dx.doi.org/10.1039/d1cc05171g.

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4

Duan, Xiaoguang, Hongqi Sun, and Shaobin Wang. "Metal-Free Carbocatalysis in Advanced Oxidation Reactions." Accounts of Chemical Research 51, no. 3 (2018): 678–87. http://dx.doi.org/10.1021/acs.accounts.7b00535.

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5

Dos Santos, Aurélie, Laurent El Kaïm, and Laurence Grimaud. "Metal-free aerobic oxidation of benzazole derivatives." Organic & Biomolecular Chemistry 11, no. 20 (2013): 3282. http://dx.doi.org/10.1039/c3ob27404g.

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6

Lou, Ji-Cong, Jian-Ye Li, Wen-Wu Sun, and Bin Wu. "Metal-Free Oxidation of Trichloroacetimidates to Aldehydes." Asian Journal of Organic Chemistry 8, no. 2 (2019): 265–68. http://dx.doi.org/10.1002/ajoc.201800683.

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7

Biswas, Swapan Kumar, and Titas Biswas. "Metal-free one-pot oxidative conversion: Molecular Iodine Mediated Oxidation Organic Reactions." International Journal of Experimental Research and Review 27 (April 30, 2022): 45–52. http://dx.doi.org/10.52756/ijerr.2022.v27.005.

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Various oxidative compounds such as aldehyde, ketone ester, and acids can be produced in large yields by an effective iodine-mediated oxidative reaction of organic molecules. Molecular iodine is a generally available and commercially extremely inexpensive substance that induces oxidative esterification. With the comparison with different Brønsted acid catalysis, molecular iodine or iodophilic activations proceed the reaction onto a deoxygenation pathway. With only a few mol% of I2, the oxidation occurs very quickly at room temperature. This approach could also be used to transport different be

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8

Zografos, Alexandros, and Marina Petsi. "Advances in Catalytic Aerobic Oxidations by Activation of Dioxygen-Monooxygenase Enzymes and Biomimetics." Synthesis 50, no. 24 (2018): 4715–45. http://dx.doi.org/10.1055/s-0037-1610297.

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Monooxygenases are not only some of the most versatile machineries in our lives, but also some of the most explored enzymes in modern organic synthesis. They provide knowledge and inspiration on how the most abandoned oxidant, dioxygen, can be activated and utilized to deliver selective oxidations. This review presents an outline in the mechanisms that Nature uses to succeed in these processes and recent indicative examples on how chemists use this knowledge to develop selective oxidation protocols based on dioxygen as the terminal oxidant.1 Introduction2 Monooxygenases2.1 Metal-Based Monooxyg

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9

Hamami, Zine Eddine, Laurent Vanoye, Pascal Fongarland, Claude de Bellefon, and Alain Favre-Reguillon. "Metal-free, visible light-promoted aerobic aldehydes oxidation." Journal of Flow Chemistry 6, no. 3 (2016): 206–10. http://dx.doi.org/10.1556/1846.2016.00023.

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10

Rahimi, Alireza, Ali Azarpira, Hoon Kim, John Ralph, and Shannon S. Stahl. "Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin." Journal of the American Chemical Society 135, no. 17 (2013): 6415–18. http://dx.doi.org/10.1021/ja401793n.

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11

Wu, Xiao-Feng, Andranik Petrosyan, Tariel V. Ghochikyan, Ashot S. Saghyan, and Peter Langer. "Metal-free oxidation of benzyl amines to imines." Tetrahedron Letters 54, no. 24 (2013): 3158–59. http://dx.doi.org/10.1016/j.tetlet.2013.04.018.

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12

Wertz, Sebastian, and Armido Studer. "Nitroxide-catalyzed transition-metal-free aerobic oxidation processes." Green Chemistry 15, no. 11 (2013): 3116. http://dx.doi.org/10.1039/c3gc41459k.

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13

Wagh, Ravindra B., and Jayashree M. Nagarkar. "A Simple Metal Free Oxidation of Sulfide Compounds." Catalysis Letters 147, no. 1 (2016): 181–87. http://dx.doi.org/10.1007/s10562-016-1932-1.

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14

Lalevée, Jacques, Sofia Telitel, Pu Xiao, et al. "Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization." Beilstein Journal of Organic Chemistry 10 (April 15, 2014): 863–76. http://dx.doi.org/10.3762/bjoc.10.83.

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In the present paper, the photoredox catalysis is presented as a unique approach in the field of photoinitiators of polymerization. The principal photocatalysts already reported as well as the typical oxidation and reduction agents used in both reductive or oxidative cycles are gathered. The chemical mechanisms associated with various systems are also given. As compared to classical iridium-based photocatalysts which are mainly active upon blue light irradiation, a new photocatalyst Ir(piq)2(tmd) (also known as bis(1-phenylisoquinolinato-N,C 2’)iridium(2,2,6,6-tetramethyl-3,5-heptanedionate) i

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15

Khodabakhshi, Saeed, Bahador Karami, Khalil Eskandari, S. Jafar Hoseini, and Alimorad Rashidi. "Graphene oxide nanosheets promoted regioselective and green synthesis of new dicoumarols." RSC Adv. 4, no. 34 (2014): 17891–95. http://dx.doi.org/10.1039/c4ra00508b.

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Graphene oxide (GO) was obtained by modified Hummers oxidation of graphite and used as a highly efficient, metal-free, non-oxidative, and recyclable catalyst to promote the condensation of 4-hydroxycoumarin and aryl glyoxals for synthesis of new dicoumarols.

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16

Gajeles, Ghellyn, Se Mi Kim, Jong-Cheol Yoo, Kyung-Koo Lee, and Sang Hee Lee. "Recyclable anhydride catalyst for H2O2 oxidation: N-oxidation of pyridine derivatives." RSC Advances 10, no. 15 (2020): 9165–71. http://dx.doi.org/10.1039/d0ra00265h.

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17

Vila, Carlos, Jonathan Lau, and Magnus Rueping. "Visible-light photoredox catalyzed synthesis of pyrroloisoquinolines via organocatalytic oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade with Rose Bengal." Beilstein Journal of Organic Chemistry 10 (May 27, 2014): 1233–38. http://dx.doi.org/10.3762/bjoc.10.122.

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Pyrrolo[2,1-a]isoquinoline alkaloids have been prepared via a visible light photoredox catalyzed oxidation/[3 + 2] cycloaddition/oxidative aromatization cascade using Rose Bengal as an organo-photocatalyst. A variety of pyrroloisoquinolines have been obtained in good yields under mild and metal-free reaction conditions.

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18

Shaik, Siddiq Pasha, Faria Sultana, A. Ravikumar, Satish Sunkari, Abdullah Alarifi, and Ahmed Kamal. "Regioselective oxidative cross-coupling of benzo[d]imidazo[2,1-b]thiazoles with styrenes: a novel route to C3-dicarbonylation." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7696–704. http://dx.doi.org/10.1039/c7ob01778b.

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Iodine promoted metal-free domino protocol has been developed for the C3-dicarbonylation of benzo[d]imidazo[2,1-b]thiazoles (IBTs) with styrenes via oxidative cleavage of the C(sp<sup>2</sup>)–H bond, followed by C3-nucleophilic attack of IBT and oxidation.

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19

Byrne, Joseph P., and Martin Albrecht. "Anion–cation synergistic metal-free catalytic oxidative homocoupling of benzylamines by triazolium iodide salts." Organic & Biomolecular Chemistry 18, no. 37 (2020): 7379–87. http://dx.doi.org/10.1039/d0ob01472a.

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Triazolium iodides are excellent catalysts for the oxidative coupling of benzylamines due to a synergistic cation/anion effect, with iodide acting as I<sup>−</sup>/I<sub>2</sub> redox manifold and the triazolium cation facilitating the iodine reduction and concomitant substrate oxidation.

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20

Wang, Zhiyong, Jie Shi, Dan Wang, Yuan Pu, Jie-Xin Wang, and Jian-Feng Chen. "Metal-free catalytic oxidation of benzylic alcohols for benzaldehyde." Reaction Chemistry & Engineering 4, no. 3 (2019): 507–15. http://dx.doi.org/10.1039/c8re00265g.

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21

Peixoto, P. A., M. Cormier, J. Ekosso Epane, A. Jean, J. Maddaluno, and M. De Paolis. "Metal-free aerobic C–H oxidation of cyclic enones." Org. Chem. Front. 1, no. 7 (2014): 748–54. http://dx.doi.org/10.1039/c4qo00125g.

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22

Dorado, Vicente, Clara I. Herrerías, and José M. Fraile. "Simple metal-free oxidative cleavage of 1,2-diols." Tetrahedron 139 (May 3, 2023): 133450. https://doi.org/10.1016/j.tet.2023.133450.

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Cleavage of 1,2-diols is easily carried out under mild conditions with the Oxone/KBr (or Oxone/NaCl) method in either acetonitrile/water or <em>tert</em>-butanol/water medium at room temperature. This procedure is highly efficient for the cleavage of dihydroxyfatty esters and acids. The reaction takes place through a double oxidation of the 1,2-diol, leading to the 1,2-diketone that undergoes a Baeyer-Villiger oxidation, with a final hydrolysis of the generated anhydride. The application to other diols, including simple internal and terminal diols, is also possible, but the nature of the diol

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23

Hou, Shengtai, Nanqing Chen, Pengfei Zhang, and Sheng Dai. "Heterogeneous viologen catalysts for metal-free and selective oxidations." Green Chemistry 21, no. 6 (2019): 1455–60. http://dx.doi.org/10.1039/c8gc03772h.

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24

Chen, Haolin, and Feng Liu. "Photo-Induced Aerobic Oxidation of C–H Bonds." Molecules 29, no. 22 (2024): 5277. http://dx.doi.org/10.3390/molecules29225277.

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The photo-induced aerobic oxidation of C–H bonds has become an increasingly valuable strategy in organic synthesis, offering a green and efficient method for introducing oxygen into organic molecules. The utilization of molecular oxygen as an oxidant, coupled with visible-light photocatalysis, has gained significant attention due to its sustainability, atom economy, and environmentally benign nature. This review highlights the recent advancements in the field, focusing on the development of metal-free and transition-metal-based photocatalytic systems and novel photosensitizers capable of promo

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25

Yang, Fan, Bihui Zhou, Pu Chen, et al. "Transition-Metal-Free C(sp3)–H Oxidation of Diarylmethanes." Molecules 23, no. 8 (2018): 1922. http://dx.doi.org/10.3390/molecules23081922.

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An efficient direct C(sp3)–H oxidation of diarylmethanes has been demonstrated by this study. This method employs environment-friendly O2 as an oxidant and is promoted by commercially available MN(SiMe3)2 [M = K, Na or Li], which provides a facile method for the synthesis of various diaryl ketones in excellent yields. This protocol is metal-free, mild and compatible with a number of functional groups on substrates.

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26

Hamano, Masaya, Kevin D. Nagy, and Klavs F. Jensen. "Continuous flow metal-free oxidation of picolines using air." Chemical Communications 48, no. 15 (2012): 2086. http://dx.doi.org/10.1039/c2cc17123f.

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27

Lambert, Kyle. "Catalytic, Metal-Free Oxidation of Primary Amines to Nitriles." Organic Syntheses 95 (2018): 60–79. http://dx.doi.org/10.15227/orgsyn.095.0060.

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28

Dos Santos, Aurelie, Laurent El Kaim, and Laurence Grimaud. "ChemInform Abstract: Metal-Free Aerobic Oxidation of Benzazole Derivatives." ChemInform 44, no. 38 (2013): no. http://dx.doi.org/10.1002/chin.201338131.

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29

Tan, Jiajing, Tianyu Zheng, Yuqi Yu, and Kun Xu. "TBHP-promoted direct oxidation reaction of benzylic Csp3–H bonds to ketones." RSC Advances 7, no. 25 (2017): 15176–80. http://dx.doi.org/10.1039/c7ra00352h.

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30

Xu, Li-Wen, Xing-Feng Bai, Guang Gao, et al. "Metal-Free Relay Oxidation: Valuable Synthesis of Acylsilane and Ketones under Aerobic Oxidation." Synlett 2011, no. 20 (2011): 3031–35. http://dx.doi.org/10.1055/s-0031-1289907.

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31

Gayakwad, Eknath M., Vilas V. Patil, and Ganapati S. Shankarling. "Nonanebis(peroxoic acid) mediated efficient and selective oxidation of sulfide." New Journal of Chemistry 40, no. 1 (2016): 223–30. http://dx.doi.org/10.1039/c5nj02616d.

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32

Fang, Xiang, Xueyan Yang, Tongle Shao, Jun Zhou, Chen Jin та Fanhong Wu. "I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage". Synlett 28, № 15 (2017): 2018–23. http://dx.doi.org/10.1055/s-0036-1588833.

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A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

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33

Sinthika, S., E. Mathan Kumar, and Ranjit Thapa. "Doped h-BN monolayer as efficient noble metal-free catalysts for CO oxidation: the role of dopant and water in activity and catalytic de-poisoning." J. Mater. Chem. A 2, no. 32 (2014): 12812–20. http://dx.doi.org/10.1039/c4ta02434f.

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34

Glavinović, Martin, Feng Qi, Athanassios D. Katsenis, Tomislav Friščić, and Jean-Philip Lumb. "Redox-promoted associative assembly of metal–organic materials." Chemical Science 7, no. 1 (2016): 707–12. http://dx.doi.org/10.1039/c5sc02214b.

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35

Sahu, Tushar Kanta, Suhaib Alam, Sourav Bhowmick, Manoj Kumar Mohanta, and Mohammad Qureshi. "Phosphorus nitride nano-dots as a versatile and metal-free support for efficient photoelectrochemical water oxidation." Chemical Communications 57, no. 50 (2021): 6157–60. http://dx.doi.org/10.1039/d1cc01030a.

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36

Rusetskaya, N. Y., and V. B. Borodulin. "Biological activity of selenorganic compounds at heavy metal salts intoxication." Biomeditsinskaya Khimiya 61, no. 4 (2015): 449–61. http://dx.doi.org/10.18097/pbmc20156104449.

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Possible mechanisms of the antitoxic action of organoselenium compounds in heavy metal poisoning have been considered. Heavy metal toxicity associated with intensification of free radical oxidation, suppression of the antioxidant system, damage to macromolecules, mitochondria and the genetic material can cause apoptotic cell death or the development of carcinogenesis. Organic selenium compounds are effective antioxidants during heavy metal poisoning; they exhibit higher bioavailability in mammals than inorganic ones and they are able to activate antioxidant defense, bind heavy metal ions and r

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37

Iida, Hiroki, Marina Oka, and Ryo Kozako. "Green Aerobic Oxidation of Thiols to Disulfides by Flavin–Iodine Coupled Organocatalysis." Synlett 32, no. 12 (2021): 1227–30. http://dx.doi.org/10.1055/a-1520-9916.

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AbstractCoupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.

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38

El-Assaad, Tarek H., Keshaba N. Parida, Marcello F. Cesario, and Dominic V. McGrath. "Sterically driven metal-free oxidation of 2,7-di-tert-butylpyrene." Green Chemistry 22, no. 18 (2020): 5966–71. http://dx.doi.org/10.1039/d0gc02000a.

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39

Sampathkumar, Suresh, and Selvarengan Paranthaman. "Neutral noble-metal-free VCoO2 and CrCoO2 cluster catalysts for CO oxidation by O2." New Journal of Chemistry 45, no. 8 (2021): 4090–100. http://dx.doi.org/10.1039/d0nj05199c.

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40

Yang, Zixu, Yang Sun, Weizhi Wang, Xiaohan Yuan, Pengfei Tian, and Jing Xu. "Dual-Mechanism Study of Metal-Free g-C3N4 Catalysts for Advanced Oxidation Under Non-Photocatalytic Conditions." Molecules 30, no. 2 (2025): 247. https://doi.org/10.3390/molecules30020247.

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Metal-free materials have been proved to be promising replacements of traditional metal-based catalysts for advanced oxidation reactions. Carbon nitride was found to be able to activate H2O2 and generate hydroxyl radicals (•OH). Nevertheless, the performance of carbon nitride is highly dependent on an external light source. In this work, we report a light-independent, metal-free catalyst based on g-C3N4 prepared using a facile calcination method. It is revealed that two reaction pathways, a radical (•OH) one and a nonradical (H2O2) one, coexist in organics oxidation on g-C3N4. The dominant rea

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41

Malekafzali, A., K. Malinovska, and F. W. Patureau. "The cumene/O2 system: a very simple tool for the radical chain oxidation of some functional groups." New Journal of Chemistry 41, no. 15 (2017): 6981–85. http://dx.doi.org/10.1039/c7nj01666b.

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42

Karimi, Babak, Mina Ghahremani, Hojatollah Vali, Rosaria Ciriminna, and Mario Pagliaro. "Aerobic oxidation and oxidative esterification of alcohols through cooperative catalysis under metal-free conditions." Chemical Communications 57, no. 71 (2021): 8897–900. http://dx.doi.org/10.1039/d1cc02937a.

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The ABNO@PMO-IL-Br material obtained by anchoring 9-azabicyclo[3.3.1]nonane-3-one N-oxyl within the mesopores of PMO with bridged imidazolium groups is a robust bifunctional catalyst for the metal-free aerobic oxidation of a wide variety of alcohols under oxygen balloon reaction conditions.

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43

Szkop, Kevin M., and Douglas W. Stephan. "Metal-free pincer ligand chemistry polycationic phosphonium Lewis acids." Dalton Transactions 46, no. 12 (2017): 3921–28. http://dx.doi.org/10.1039/c7dt00441a.

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Oxidation with or without subsequent methylation of the pyridine of 2,6-bis(diphenylphosphine)methyl pyridine affords di- and tricationic phosphonium salts. These species are used as Lewis acid catalysts for the dimerization of 1,1-diphenylethylene, the hydrodefluorination of 1-fluoroadamantane, and the dehydrocoupling of phenol and silane.

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44

Liu, Kai, Guangyang Xu, and Jiangtao Sun. "Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles." Chemical Science 9, no. 3 (2018): 634–39. http://dx.doi.org/10.1039/c7sc04086e.

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45

Hazra, Susanta, Mayukh Deb, and Anil J. Elias. "Iodine catalyzed oxidation of alcohols and aldehydes to carboxylic acids in water: a metal-free route to the synthesis of furandicarboxylic acid and terephthalic acid." Green Chemistry 19, no. 23 (2017): 5548–52. http://dx.doi.org/10.1039/c7gc02802d.

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46

Hu, Ben-Quan, Jie Cui, Li-Xia Wang, Ya-Lin Tang, and Luo Yang. "Metal-free synthesis of quinazolinones without any additives in water." RSC Advances 6, no. 50 (2016): 43950–53. http://dx.doi.org/10.1039/c6ra05777b.

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Here we report that an excess amount of aldehyde, in particular, aliphatic aldehyde, without any additives, efficiently facilitates the oxidation of aminal intermediates to quinazolinones in pure water.

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47

Luňák, Stanislav, Marie Vašková, and Pavel Lederer. "Oxidation of 1,2,3,4-tetrahydronaphthalene by dioxygen. Effect of the free radical initiators 1,2,3,4-tetrahydro-1-naphthylhydroperoxide and 2,2'-azobis(2-methylpropionitrile) on the reaction catalyzed by 2,4-pentanedionates of 3d transition metals." Collection of Czechoslovak Chemical Communications 55, no. 4 (1990): 1015–21. http://dx.doi.org/10.1135/cccc19901015.

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The effect of the free radical initiators 1,2,3,4-tetrahydro-1-naphthylhydroperoxide and 2,2'-azobis(2-methylpropionitrile) on the oxidation of 1,2,3,4-tetrahydronaphthalene (tetraline) by dioxygen catalyzed by Cr(III), Mn(III), Fe(III), Co(II), Co(III) and Cu(II) 2,4-pentanedionates (acac) has been investigated. It has been found that the addition of a free radical initiator can increase the rate of catalyzed oxidation or decrease it. Which effect will operate depends on the kind of the catalyzing transition metal ion and its oxidation state. The results obtained indicate that the above free

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48

Bian, Mixue, Jiawei Hua, Tao Ma, et al. "Continuous-flow electrosynthesis of selenium-substituted iminoisobenzofuran via oxidative cyclization of olefinic amides and diselenides." Organic & Biomolecular Chemistry 19, no. 14 (2021): 3207–12. http://dx.doi.org/10.1039/d1ob00236h.

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A novel method for the continuous synthesis of selenated iminoisobenzofurans by cyclization of olefinic amides with diselenides through electrochemical oxidation under metal-free and oxidant-free conditions has been developed.

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49

Gaspa, Silvia, Andrea Porcheddu, and Lidia De Luca. "Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA." Organic Letters 17, no. 15 (2015): 3666–69. http://dx.doi.org/10.1021/acs.orglett.5b01579.

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50

Mittal, Neha, Grace M. Nisola, Lenny B. Malihan, Jeong Gil Seo, Seong-Poong Lee, and Wook-Jin Chung. "Metal-free mild oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran." Korean Journal of Chemical Engineering 31, no. 8 (2014): 1362–67. http://dx.doi.org/10.1007/s11814-014-0036-0.

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