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Journal articles on the topic 'Metal-free oxidation'

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Published: 9 March 2023
Last updated: 10 March 2023

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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 (June 12, 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 Introduction2 Methods of Preparation of Cyclic Diacyl Peroxides3 Structures and Stabilities of Cyclic Diacyl Peroxides4 Oxidation Reactions4.1 Oxidative Additions to Alkenes4.2 Oxidation Reactions of Heteroatoms4.3 Oxidation Reactions of 1,3-Dicarbonyl Compounds4.4 Hydroxylations of Arenes5 Decarboxylations6 Conclusion
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3

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

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4

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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5

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 (January 18, 2019): 265–68. http://dx.doi.org/10.1002/ajoc.201800683.

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6

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 benzil derivatives from nonactivated alkynes, such as diaryl acetylenes. Molecular iodine with several mild reagents such as aq. NH3, ∼30% aq. H2O2 and DMSO might be used to convert various one degree alcohols, particularly benzylic alcohols, into the corresponding aromatic amides in suffiently high yields in a one-pot method. Similarly, by treating different benzylic chloride, bromide and iodide with a molecular iodine oxidation medium, the corresponding aromatic amides may be prepared in a one-pot method. The reactions in this section include transformation of several compounds into their respective oxidative products with the metal-free one-pot oxidative.
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7

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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8

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 (September 2016): 206–10. http://dx.doi.org/10.1556/1846.2016.00023.

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9

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 (April 19, 2013): 6415–18. http://dx.doi.org/10.1021/ja401793n.

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10

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 (June 2013): 3158–59. http://dx.doi.org/10.1016/j.tetlet.2013.04.018.

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11

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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12

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

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13

Zografos, Alexandros, and Marina Petsi. "Advances in Catalytic Aerobic Oxidations by Activation of Dioxygen-Monooxygenase Enzymes and Biomimetics." Synthesis 50, no. 24 (October 15, 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 Monooxygenases2.1.1 Cytochromes2.1.2 Copper-Dependent Monooxygenases2.1.3 Heme-Independent Iron Monooxygenases2.1.4 Pterin-Dependent Monooxygenases2.2 Metal-Free Monooxygenases2.2.1 Flavin-Dependent Monooxygenases2.2.2 Systems without Cofactors3 Biomimetic Aerobic Oxidations3.1 Aerobic Oxidations Based on Metal Catalysts3.1.1 Epoxidations and Allylic Oxidations3.1.2 Oxidations of Unactivated Carbon Atoms and Benzylic Oxidations3.1.3 Oxidations of Aryl Groups3.1.4 Heteroatom Oxidations3.2 Aerobic Oxidations Based on Organocatalysts3.2.1 Baeyer–Villiger Oxidations3.2.2 Oxidations of Aryl Groups3.2.3 Heteroatom Oxidations4 Conclusion
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14

Lalevée, Jacques, Sofia Telitel, Pu Xiao, Marc Lepeltier, Frédéric Dumur, Fabrice Morlet-Savary, Didier Gigmes, and Jean-Pierre Fouassier. "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) is also proposed as an example of green light photocatalyst (toward the long wavelength irradiation). The chemical mechanisms associated with Ir(piq)2(tmd) are investigated by ESR spin-trapping, laser flash photolysis, steady state photolysis, cyclic voltammetry and luminescence experiments.
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15

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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16

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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17

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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18

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−/I2 redox manifold and the triazolium cation facilitating the iodine reduction and concomitant substrate oxidation.
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19

Yang, Fan, Bihui Zhou, Pu Chen, Dong Zou, Qiannan Luo, Wenzhe Ren, Linlin Li, Limei Fan, and Jie Li. "Transition-Metal-Free C(sp3)–H Oxidation of Diarylmethanes." Molecules 23, no. 8 (August 1, 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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20

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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21

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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22

Dos Santos, Aurelie, Laurent El Kaim, and Laurence Grimaud. "ChemInform Abstract: Metal-Free Aerobic Oxidation of Benzazole Derivatives." ChemInform 44, no. 38 (August 30, 2013): no. http://dx.doi.org/10.1002/chin.201338131.

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23

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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24

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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25

Xu, Li-Wen, Xing-Feng Bai, Guang Gao, Zhan-Jiang Zheng, Fei Li, Guo-Qiao Lai, Kezhi Jiang, and Fuwei Li. "Metal-Free Relay Oxidation: Valuable Synthesis of Acylsilane and Ketones under Aerobic Oxidation." Synlett 2011, no. 20 (November 23, 2011): 3031–35. http://dx.doi.org/10.1055/s-0031-1289907.

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26

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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27

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(sp2)–H bond, followed by C3-nucleophilic attack of IBT and oxidation.
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28

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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29

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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30

Gaspa, Silvia, Andrea Porcheddu, and Lidia De Luca. "Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA." Organic Letters 17, no. 15 (July 10, 2015): 3666–69. http://dx.doi.org/10.1021/acs.orglett.5b01579.

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31

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 (April 5, 2014): 1362–67. http://dx.doi.org/10.1007/s11814-014-0036-0.

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32

Lan, Jie, Daizong Qi, Jie Song, Peng Liu, Yi Liu, and Yun-Xiang Pan. "Noble-metal-free cobalt hydroxide nanosheets for efficient electrocatalytic oxidation." Frontiers of Chemical Science and Engineering 14, no. 6 (April 8, 2020): 948–55. http://dx.doi.org/10.1007/s11705-020-1920-2.

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33

Rocha, Raquel P., Manuel Fernando R. Pereira, and José L. Figueiredo. "Metal-free carbon materials as catalysts for wet air oxidation." Catalysis Today 356 (October 2020): 189–96. http://dx.doi.org/10.1016/j.cattod.2019.04.047.

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34

Wu, Jianglong, Yan Liu, Xiaowei Ma, Ping Liu, Chengzhi Gu, and Bin Dai. "Metal-free oxidation of secondary benzylic alcohols using aqueous TBHP." Synthetic Communications 46, no. 21 (October 14, 2016): 1747–58. http://dx.doi.org/10.1080/00397911.2016.1223307.

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35

Gupta, Neeraj, Oleksiy Khavryuchenko, Alberto Villa, and Dangsheng Su. "Metal-Free Oxidation of Glycerol over Nitrogen-Containing Carbon Nanotubes." ChemSusChem 10, no. 15 (July 18, 2017): 3030–34. http://dx.doi.org/10.1002/cssc.201700940.

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36

Wu, Xiao-Feng, Andranik Petrosyan, Tariel V. Ghochikyan, Ashot S. Saghyan, and Peter Langer. "ChemInform Abstract: Metal-Free Oxidation of Benzyl Amines to Imines." ChemInform 44, no. 39 (September 5, 2013): no. http://dx.doi.org/10.1002/chin.201339061.

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37

Wertz, Sebastian, and Armido Studer. "ChemInform Abstract: Nitroxide-Catalyzed Transition-Metal-Free Aerobic Oxidation Processes." ChemInform 45, no. 4 (January 3, 2014): no. http://dx.doi.org/10.1002/chin.201404229.

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38

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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39

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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40

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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41

Iida, Hiroki, Marina Oka, and Ryo Kozako. "Green Aerobic Oxidation of Thiols to Disulfides by Flavin–Iodine Coupled Organocatalysis." Synlett 32, no. 12 (May 31, 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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42

Wu, Ping, Pan Du, Hui Zhang, and Chenxin Cai. "Graphdiyne as a metal-free catalyst for low-temperature CO oxidation." Phys. Chem. Chem. Phys. 16, no. 12 (2014): 5640–48. http://dx.doi.org/10.1039/c3cp55121k.

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43

Kim, Sun Min, Hun Yi Shin, Dong Wan Kim, and Jung Woon Yang. "Metal-Free Chemoselective Oxidative Dehomologation or Direct Oxidation of Alcohols: Implication for Biomass Conversion." ChemSusChem 9, no. 3 (December 18, 2015): 241–45. http://dx.doi.org/10.1002/cssc.201501359.

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44

Kim, Sun Min, Hun Yi Shin, Dong Wan Kim, and Jung Woon Yang. "Metal-Free Chemoselective Oxidative Dehomologation or Direct Oxidation of Alcohols: Implication for Biomass Conversion." ChemSusChem 9, no. 3 (February 2016): 233. http://dx.doi.org/10.1002/cssc.201600098.

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45

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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46

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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47

Fang, Xiang, Xueyan Yang, Tongle Shao, Jun Zhou, Chen Jin, and Fanhong Wu. "I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage." Synlett 28, no. 15 (May 16, 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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48

Shen, Duyi, Hongyan Wang, Yanan Zheng, Xinjing Zhu, Peiwei Gong, Bin Wang, Jinmao You, Yulei Zhao, and Mianran Chao. "Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation." Journal of Organic Chemistry 86, no. 7 (March 25, 2021): 5354–61. http://dx.doi.org/10.1021/acs.joc.0c03010.

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49

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 reactive oxygen species formed during metal-induced oxidative stress. One of promising organoselenium compounds is diacetophenonyl selenide (DAPS-25), which is characterized by antioxidant and antitoxic activity, under conditions including heavy metal intoxication
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50

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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