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Journal articles on the topic 'Oxidative coupling of phenols'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Kidwai, Mazaahir, Arti Jain, Abha Sharma, and Ramesh Chander Kuhad. "Ecofriendly approach for detection of phenols in water using laccase from different fungi." Water Science and Technology 66, no. 2 (2012): 385–93. http://dx.doi.org/10.2166/wst.2012.198.

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Laccase-initiated oxidative coupling reactions of phenol and its derivatives with 4-aminoantipyrene using air as an oxidant has been investigated. The oxidation reaction of phenols and 4-aminoantipyrene is getting a lot of attention due to environmental concerns. Oxidation of simple phenol and 4-aminoantipyrene as a benchmark reaction enabled us to rank the relative oxidation ability of various laccases. Among the laccases tested, laccase from Pycnoporus cinnabarinus successfully yielded 72% antipyrilquinoneimine dye. The present method can also be used to determine p-substituted phenols and c

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2

He, Zhen, Gregory J. P. Perry, and David J. Procter. "Sulfoxide-mediated oxidative cross-coupling of phenols." Chemical Science 11, no. 7 (2020): 2001–5. http://dx.doi.org/10.1039/c9sc05668h.

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3

Takizawa, Shinobu, Junpei Kodera, Yasushi Yoshida, et al. "Enantioselective oxidative-coupling of polycyclic phenols." Tetrahedron 70, no. 9 (2014): 1786–93. http://dx.doi.org/10.1016/j.tet.2014.01.017.

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4

Dec, Jerzy, and Jean Marc Bollag. "Dehalogenation of Chlorinated Phenols during Oxidative Coupling." Environmental Science & Technology 28, no. 3 (1994): 484–90. http://dx.doi.org/10.1021/es00052a022.

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5

Kang, Houng, Young Eun Lee, Peddiahgari Vasu Govardhana Reddy, et al. "Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles." Organic Letters 19, no. 20 (2017): 5505–8. http://dx.doi.org/10.1021/acs.orglett.7b02552.

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6

Hay, Allan S. "Polymerization by oxidative coupling. II. Oxidation of 2,6-disubstituted phenols." Journal of Polymer Science Part A: Polymer Chemistry 34, no. 8 (1996): 1373–83. http://dx.doi.org/10.1002/pola.1996.829.

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7

Jiang, Qing, Wenbing Sheng, Mi Tian, Jie Tang, and Cancheng Guo. "Cobalt(II)-Porphyrin-Catalyzed Aerobic Oxidation: Oxidative Coupling of Phenols." European Journal of Organic Chemistry 2013, no. 10 (2013): 1861–66. http://dx.doi.org/10.1002/ejoc.201201595.

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8

Truchan, Nadina, Christian Jandl, Alexander Pöthig, Stefan Breitenlechner, and Thorsten Bach. "Access to Biphenyls by Palladium-Catalyzed Oxidative Coupling of Phenyl Carbamates and Phenols." Synthesis 51, no. 16 (2019): 3060–76. http://dx.doi.org/10.1055/s-0037-1611482.

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The oxidative cross-coupling of phenols (3 equiv) to various substituted phenyl N,N-diethylcarbamates was explored with a variety of substrates. Pd(OAc)2 was employed as the catalyst (20 mol%) and K2S2O8 as the stoichiometric oxidant in trifluoroacetic acid as the solvent (50 °C, 2 h). Carbamates without or with a substituent on the phenyl ring (Me, Ph, Cl, OMe) underwent the reaction unless the phenyl substituent was too strongly electron withdrawing (CN). Cross-coupling occurred exclusively in the ortho position relative to the carbamate group. The regioselectivity at the phenol (ortho or pa

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9

Nagaraju, Karre, and Dawei Ma. "Oxidative coupling strategies for the synthesis of indole alkaloids." Chemical Society Reviews 47, no. 21 (2018): 8018–29. http://dx.doi.org/10.1039/c8cs00305j.

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10

Takizawa, Shinobu, Junpei Kodera, Yasushi Yoshida, et al. "ChemInform Abstract: Enantioselective Oxidative-Coupling of Polycyclic Phenols." ChemInform 45, no. 31 (2014): no. http://dx.doi.org/10.1002/chin.201431033.

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11

Neufeldt, Sharon R., and John E. A. Russell. "C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives." Synlett 32, no. 15 (2021): 1484–91. http://dx.doi.org/10.1055/a-1503-6330.

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AbstractChemoselective cross-coupling of phenol derivatives is valuable for generating products that retain halides. Here we discuss recent developments in selective cross-couplings of chloroaryl phenol derivatives, with a particular focus on reactions of chloroaryl tosylates. The first example of a C–O-selective Ni-catalyzed Suzuki–Miyaura coupling of chloroaryl tosylates is discussed in detail.1 Introduction2 Density Functional Theory Studies on Oxidative Addition at Nickel(0)3 Stoichiometric Oxidative Addition Studies4 Development of a Tosylate-Selective Suzuki Coupling5 Conclusion and Outl

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12

Duguet, J. P., B. Dussert, J. Mallevialle, and F. Fiessinger. "Polymerization Effects of Ozone: Applications to the Removal of Phenolic Compounds from Industrial Wastewaters." Water Science and Technology 19, no. 5-6 (1987): 919–30. http://dx.doi.org/10.2166/wst.1987.0270.

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Degradation of phenols by ozone has been extensively studied but the oxidative coupling pathway of ozone resulting in a phenol polymerization has not been largely investigated. Application of low ozone dose in solutions of 2.4 dichlorophenol and salicylic acid is characterized by the formation of high molecular compounds which are partially insoluble. Numerous polymers have been identified by gas chromatography coupled with mass spectrometry. Application of the polymerization effect of ozone to petrochemical and coking wastewaters containing phenols give similar results. In each case, phenolic

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13

Makhova, T. M., A. I. Arzhanukhina, and S. Yu Doronin. "Institute of Chemistry, Chernyshevsky Saratov State University." Журнал аналитической химии 78, no. 10 (2023): 953–60. http://dx.doi.org/10.31857/s0044450223100134.

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New test tools made of nanofibers based on polyamide-6 (PA-6) for the sorption preconcentration of some phenols as their azo derivatives followed by colorimetric determination are obtained. Approaches to the derivatization of phenol and chlorine derivatives by azo coupling with 4-nitrophenyldiazonium and oxidative condensation with 4-aminoantipyrine for improving the sorption characteristics of the studied phenols are proposed. The efficiency of the two derivatization methods is compared. The sorption kinetics of phenol and 2-chlorophenol derivatives and the effect of pH on the nature of their

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14

Gilmartin, Philip H., and Marisa C. Kozlowski. "Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products." Organic Letters 22, no. 8 (2020): 2914–19. http://dx.doi.org/10.1021/acs.orglett.0c00577.

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15

Grant-Overton, Sharday, Joshua A. Buss, Eva H. Smith, et al. "Efficient Microwave Method for the Oxidative Coupling of Phenols." Synthetic Communications 45, no. 3 (2014): 331–37. http://dx.doi.org/10.1080/00397911.2014.956370.

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16

Kshirsagar, Umesh A., Clil Regev, Regev Parnes, and Doron Pappo. "Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Alkenes." Organic Letters 15, no. 12 (2013): 3174–77. http://dx.doi.org/10.1021/ol401532a.

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17

More, Nagnath Yadav, and Masilamani Jeganmohan. "Oxidative Cross-Coupling of Substituted Phenols with Unactivated Aromatics." European Journal of Organic Chemistry 2017, no. 29 (2017): 4305–12. http://dx.doi.org/10.1002/ejoc.201700666.

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18

Jiang, Qing, Wenbing Sheng, Mi Tian, Jie Tang, and Cancheng Guo. "ChemInform Abstract: Cobalt(II)-Porphyrin-Catalyzed Aerobic Oxidation: Oxidative Coupling of Phenols." ChemInform 44, no. 35 (2013): no. http://dx.doi.org/10.1002/chin.201335083.

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19

Aggarwal, Sakshi, Dasari Srinivas, Chinnabattigalla Sreenivasulu, and Gedu Satyanarayana. "Nickel catalyzed intramolecular oxidative coupling: synthesis of 3-aryl benzofurans." RSC Advances 10, no. 37 (2020): 22264–72. http://dx.doi.org/10.1039/d0ra03071f.

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We have developed nickel-catalyzed synthesis of 3-aryl benzofurans from ortho-alkenyl phenols via intramolecular dehydrogenative coupling. O<sub>2</sub> gas served as an oxidant and 3-aryl benzofurans were synthesized in good to very good yields.

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20

P., L. Majumder, Chakraborty S., and Roychowdhury M. "Catalytic aerobic oxidative coupling of some simple phenols and natural phenanthrols with CuCI(OH).TMEDA." Journal of Indian Chemical Society Vol. 77, Aug 2000 (2000): 389–93. https://doi.org/10.5281/zenodo.5868904.

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Department of Chemistry, University College of Science, University ot Calcutta, 92 Achaiya Prafulla Chandra Road. Calcutta-700 009, India <em>Manuscript received 21 january 2000. accepted 6 April 2000</em> Aerobic oxidative coupling of phenol, catechol, resorcinol and pyrogallol with CuCI(OH).TMEDA as catalyst affords 2',4- dihydroxybiphenyl (1a), 3,3',4,4'-tetrahydroxy biphenyl (2d), 2,2',4.4'-tetrahydroxybiphenyl (3a) and 2,2',4,6'-tetrahydroxybiphenyI (4a) and 2`,3,3',4,4',5-hexahydroxybiphenyl (5a), respectively, in moderate yields. Similar cat

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21

Canesi, Sylvain. "Rapid Formation of Advanced Scaffolds from Phenols and Anilines." Synlett 30, no. 06 (2018): 647–64. http://dx.doi.org/10.1055/s-0037-1610340.

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This article is an account of our efforts over the last decade to functionalize phenols and anilines at any position and to use these compounds to generate substituted aromatic systems and advanced unsaturated cyclohexanone moieties, enabling the rapid formation of complex structures. Total syntheses of numerous natural products involving such intermediates were achieved.1 Introduction2 ortho-Functionalization of Phenols and Aniline Derivatives Mediated by Iodanes (III) and Synthesis of Panacene2.1 Cross-Coupling with Aniline Derivatives2.2 Dearomative Cycloaddition of Arenes and Heteroarenes2

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22

Xu, Wei, and Boris J. Nachtsheim. "TBAI-Catalyzed Oxidative Cross-Coupling of Phenols and 2-Aminoacetophenones." Organic Letters 17, no. 6 (2015): 1585–88. http://dx.doi.org/10.1021/acs.orglett.5b00466.

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23

Tanaka, Koichi, and Fumio Toda. "Oxidative Coupling Reactions of Phenols with FeCl3in the Solid State." Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics 187, no. 1 (1990): 49–52. http://dx.doi.org/10.1080/00268949008036026.

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24

Morimoto, Koji, Kazuma Sakamoto, Yusuke Ohnishi, et al. "ChemInform Abstract: Metal-Free Oxidative para Cross-Coupling of Phenols." ChemInform 44, no. 47 (2013): no. http://dx.doi.org/10.1002/chin.201347066.

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25

Xu, Zhanwei, Xiaoqiang Yu, Xiujuan Feng та Ming Bao. "Arylglycine-derivative synthesis via oxidative sp3 C–H functionalization of α-amino esters". Beilstein Journal of Organic Chemistry 8 (18 вересня 2012): 1564–68. http://dx.doi.org/10.3762/bjoc.8.178.

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An efficient method for the synthesis of arylglycine derivatives is described. The oxidative coupling reactions of naphthols and phenols with α-amino esters proceeded smoothly in the presence of meta-chloroperoxybenzoic acid as an oxidant under ambient conditions, to produce arylglycine derivatives in satisfactory yields.

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26

Waldvogel, Siegfried R. "Novel anodic concepts for the selective phenol coupling reaction." Pure and Applied Chemistry 82, no. 4 (2010): 1055–63. http://dx.doi.org/10.1351/pac-con-09-10-21.

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The oxidative phenol coupling reaction of phenols with simple methyl substituents can be difficult due to several by-products. Such a challenging substrate is 2,4-dimethyl-phenol. We studied the electrochemical access to the ortho-coupled dehydrodimer. Anodic treatment in a basic electrolyte supports the formation of a molecular tricyclic architecture called Pummerer’s ketone. Employing a two-step sequence involving anodic conversion of 2,4-dimethylphenol to a preliminary substrate and different workup protocols yield exclusively and diastereoselectively polycyclic architectures. The selective

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27

Niederer, Kyle A., Philip H. Gilmartin, and Marisa C. Kozlowski. "Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine." ACS Catalysis 10, no. 24 (2020): 14615–23. http://dx.doi.org/10.1021/acscatal.0c04515.

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28

Kupwade, Ravindra V. "A Concise Review of Hypervalent Iodine with Special Reference to Dess- Martin Periodinane." Mini-Reviews in Organic Chemistry 17, no. 8 (2020): 946–57. http://dx.doi.org/10.2174/1570193x17666200221124739.

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The chemistry of hypervalent iodine compounds has been experiencing considerable attention of organic chemists during the past few years. Hypervalent iodine reagents have found ubiquitous applications in organic synthesis because of their mild and highly chemoselective oxidizing properties, easy commercial availability, and environmental benign character. Along with oxidation of alcohol, they have also shown to be useful in number of organic transformations which include oxidative functionalization of carbonyl compounds, catalytic imidations, cyclization, oxidative coupling of phenols, amines

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29

More, Nagnath Yadav, and Masilamani Jeganmohan. "Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols." Chemical Communications 53, no. 69 (2017): 9616–19. http://dx.doi.org/10.1039/c7cc04829g.

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A regioselective synthesis of unsymmetrical and symmetrical biphenols and binaphtholsviaoxidative coupling of phenols or naphthols in the presence of K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>in CF<sub>3</sub>COOH under ambient conditions is described.

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30

Vincent, Guillaume, Natacha Denizot, Régis Guillot, and Cyrille Kouklovsky. "N-Iodosuccinimide-Mediated Oxidative Coupling of Indoles and Phenols: A Synthetic Study toward the Benzofuroindoline Moiety of Bipleiophylline." Synthesis 50, no. 24 (2018): 4823–28. http://dx.doi.org/10.1055/s-0036-1592002.

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We report our efforts to apply an N-iodosuccinimide-mediated dearomative oxidative coupling of indoles and phenols to benzofuroindoline-containing polycyclic scaffolds related to the natural product bipleiophylline. Suitable conditions from N-substituted indoles are developed and applied to the synthesis of a hexacyclic model starting from a tetracyclic ABCE precursor.

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31

Lee, Young Eun, Trung Cao, Carilyn Torruellas, and Marisa C. Kozlowski. "Selective Oxidative Homo- and Cross-Coupling of Phenols with Aerobic Catalysts." Journal of the American Chemical Society 136, no. 19 (2014): 6782–85. http://dx.doi.org/10.1021/ja500183z.

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32

Shalit, Hadas, Anna Libman, and Doron Pappo. "meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols." Journal of the American Chemical Society 139, no. 38 (2017): 13404–13. http://dx.doi.org/10.1021/jacs.7b05898.

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33

Vidic, Radisav D., Makram T. Suidan, and Richard C. Brenner. "Oxidative coupling of phenols on activated carbon: impact on adsorption equilibrium." Environmental Science & Technology 27, no. 10 (1993): 2079–85. http://dx.doi.org/10.1021/es00047a013.

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34

Huang, Zhiliang, Liqun Jin, Ye Feng, Pan Peng, Hong Yi, and Aiwen Lei. "Iron-Catalyzed Oxidative Radical Cross-Coupling/Cyclization between Phenols and Olefins." Angewandte Chemie 125, no. 28 (2013): 7292–96. http://dx.doi.org/10.1002/ange.201210023.

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35

Kshirsagar, Umesh A., Clil Regev, Regev Parnes, and Doron Pappo. "ChemInform Abstract: Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Alkenes." ChemInform 44, no. 47 (2013): no. http://dx.doi.org/10.1002/chin.201347083.

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36

Grant-Overton, Sharday, Joshua A. Buss, Eva H. Smith, et al. "ChemInform Abstract: Efficient Microwave Method for the Oxidative Coupling of Phenols." ChemInform 46, no. 20 (2015): no. http://dx.doi.org/10.1002/chin.201520101.

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37

Huang, Zhiliang, Liqun Jin, Ye Feng, Pan Peng, Hong Yi, and Aiwen Lei. "Iron-Catalyzed Oxidative Radical Cross-Coupling/Cyclization between Phenols and Olefins." Angewandte Chemie International Edition 52, no. 28 (2013): 7151–55. http://dx.doi.org/10.1002/anie.201210023.

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38

Wu, Yun-Bin, Dan Xie, Zhong-Lin Zang, Cheng-He Zhou, and Gui-Xin Cai. "Palladium-catalyzed aerobic regio- and stereo-selective olefination reactions of phenols and acrylatesviadirect dehydrogenative C(sp2)–O cross-coupling." Chemical Communications 54, no. 35 (2018): 4437–40. http://dx.doi.org/10.1039/c8cc01226a.

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39

Mokhtari, Javad, Kamelia Madankar, and Zohreh Mirjafary. "A Novel Modified Cross-Coupling of Phenols and Amines Using Dichloroimidazolidinedione (DCID)." Synlett 31, no. 17 (2020): 1725–29. http://dx.doi.org/10.1055/s-0040-1707224.

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Phenols are considered as an ideal alternative to aryl halides as coupling partners in cross-coupling reactions. In the present work a copper-catalyzed cross-coupling of phenols with various aromatic and aliphatic amines for the synthesis of secondary aryl amines using dichloroimidazolidinedione (DCID) as a new and efficient activating agent has been developed. Substituted phenols were compatible with the standard reaction conditions. The two proposed mechanisms, which are based on the oxidation addition of copper with Ar-OMCID (MCID: Monochloroimidazolidinedione), are also discussed.

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40

Barton, Richard J., Keith E. Johnson, Beverly E. Robertson, F. Wayne Yerhoff, and Shengzhi Hu. "Structures of the pyrazolones formed by oxidative coupling of phenols with 4-aminoantipyrine." Canadian Journal of Chemistry 65, no. 9 (1987): 2082–88. http://dx.doi.org/10.1139/v87-345.

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The structures of reaction products between 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and o-cresol, p-cresol, and p-ethylphenol are reported. The reaction of the former compound with phenols is used to estimate the concentration of phenol in potable water supplies. The reaction products are 2,3-dimethyl-4-[4-oxo-2,5-cyclohexadien-1-ylidene)amino]-1-phenyl-3-pyrazolin-5-one (monoclinic, P21/c, red, Z = 4, a = 7.092(1), b = 26.616(2), c = 8.644(2) Å, β = 79.17(3)°, 1432 reflections, R = 0.083, Rw = 0.040), 1,9a-dihydro-1,6,9a-trimethyl-2-phenylpyrazolo[3,4-b][1,4]benzoxazin-3(2H)-one (orth

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41

Lund, M., and A. J. Ragauskas. "Enzymatic modification of kraft lignin through oxidative coupling with water-soluble phenols." Applied Microbiology and Biotechnology 55, no. 6 (2001): 699–703. http://dx.doi.org/10.1007/s002530000561.

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42

Xu, Wei, and Boris J. Nachtsheim. "ChemInform Abstract: TBAI-Catalyzed Oxidative Cross-Coupling of Phenols and 2-Aminoacetophenones." ChemInform 46, no. 32 (2015): no. http://dx.doi.org/10.1002/chin.201532195.

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43

Mintz, Tomer, Nagnath Yadav More, Eden Gaster, and Doron Pappo. "Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles." Journal of Organic Chemistry 86, no. 24 (2021): 18164–78. http://dx.doi.org/10.1021/acs.joc.1c02435.

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44

Xia, Wujiong, Yating Zhao, Binbin Huang, Chao Yang, and Bing Li. "Metal-Free [3+2] Oxidative Coupling of Phenols with Alkenes: Synthesis of Dihydrobenzofurans." Synthesis 47, no. 18 (2015): 2731–37. http://dx.doi.org/10.1055/s-0034-1380419.

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45

Hwang, Der-Ren, Cheu-Pyeng Chen, and Biing-Jiun Uang. "Aerobic catalytic oxidative coupling of 2-naphthols and phenols by VO(acac)2." Chemical Communications, no. 13 (1999): 1207–8. http://dx.doi.org/10.1039/a901934k.

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46

Marques, Francisco A., Fabio Simonelli, Alfredo R. M. Oliveira, George L. Gohr, and Paulo C. Leal. "Oxidative coupling of 4-substituted 2-methoxy phenols using methyltributylammonium permanganate in dichloromethane." Tetrahedron Letters 39, no. 9 (1998): 943–46. http://dx.doi.org/10.1016/s0040-4039(97)10665-7.

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47

Toda, Fumio, Koichi Tanaka, and Shinji Iwata. "Oxidative coupling reactions of phenols with iron(III) chloride in the solid state." Journal of Organic Chemistry 54, no. 13 (1989): 3007–9. http://dx.doi.org/10.1021/jo00274a007.

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48

Dyadyuk, Alina, Kavitha Sudheendran, Yulia Vainer, Vlada Vershinin, Alexander I. Shames, and Doron Pappo. "Direct Synthesis of Polyaryls by Consecutive Oxidative Cross-Coupling of Phenols with Arenes." Organic Letters 18, no. 17 (2016): 4324–27. http://dx.doi.org/10.1021/acs.orglett.6b02064.

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49

Zhao, Yating, Binbin Huang, Chao Yang, and Wujiong Xia. "Visible-Light-Promoted Direct Amination of Phenols via Oxidative Cross-Dehydrogenative Coupling Reaction." Organic Letters 18, no. 14 (2016): 3326–29. http://dx.doi.org/10.1021/acs.orglett.6b01371.

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50

More, Nagnath Yadav, and Masilamani Jeganmohan. "Oxidative Cross-Coupling of Two Different Phenols: An Efficient Route to Unsymmetrical Biphenols." Organic Letters 17, no. 12 (2015): 3042–45. http://dx.doi.org/10.1021/acs.orglett.5b01324.

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