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Journal articles on the topic 'Electrogenerated base'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Suzuki, Shohei, Mitsuko Kato, and Shoichi Nakajima. "Application of electrogenerated triphenylmethyl anion as a base for alkylation of arylacetic esters and arylacetonitriles and isomerization of allylbenzenes." Canadian Journal of Chemistry 72, no. 2 (1994): 357–61. http://dx.doi.org/10.1139/v94-055.

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Phenylacetic esters and phenylacetonitriles were alkylated with alkyl halides, at the position α to an ester or nitrile, either at room temperature (20 °C) or at −78 °C, by making use of electrogenerated triphenylmethyl anion (trityl anion). Double-bond isomerization of allylbenzenes was also effectively accomplished by use of this electrogenerated base (EGB).

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2

Liu, Tongjun, and Zhenglong Li. "An electrogenerated base for the alkaline oxidative pretreatment of lignocellulosic biomass to produce bioethanol." RSC Adv. 7, no. 75 (2017): 47456–63. http://dx.doi.org/10.1039/c7ra08101d.

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3

Bousfiha, Asmae, Abdou K. D. Dimé, Amelle Mankou-Makaya, et al. "Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation." Chemical Communications 56, no. 6 (2020): 884–87. http://dx.doi.org/10.1039/c9cc07351e.

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Four free base aminoporphyrins were synthesized in two steps via regioselective anodic nucleophilic substitution with pyridine followed by ring opening of the electrogenerated pyridinium with piperidine.

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4

Picazo, O., B. Batanero, and F. Barba. "Cathodic Reduction of O-Ethyl S-Phenacyl Dithiocarbonate." Journal of Chemical Research 2000, no. 7 (2000): 332–33. http://dx.doi.org/10.3184/030823400103167525.

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The cathodic reduction of O-ethyl S-phenacyl dithiocarbonate (1) yields O-ethyl (benzoyl)-thioacetate (2) and O-ethyl S-[(ethoxythiocarbonyl)(phenacyl)]-dithiocarbonate (3) through an Eschenmoser process with an electrogenerated base (EGB).

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5

Matsumura, Yoshimasa, Yoshinobu Kakizaki, Hiroyuki Tateno, Tsuneo Kashiwagi, Yoshiyuki Yamaji, and Mahito Atobe. "Continuous in situ electrogenaration of a 2-pyrrolidone anion in a microreactor: application to highly efficient monoalkylation of methyl phenylacetate." RSC Advances 5, no. 117 (2015): 96851–54. http://dx.doi.org/10.1039/c5ra19286b.

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We have successfully demonstrated effective generation of an electrogenerated base (EGB) such as the 2-pyrrolidone anion and its rapid use for the following alkylation reaction in a flow microreactor system without the need for severe reaction conditions.

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6

Choi, Jai-Pil, and Allen J. Bard. "Electrogenerated chemiluminescence 73: acid–base properties, electrochemistry, and electrogenerated chemiluminescence of neutral red in acetonitrile." Journal of Electroanalytical Chemistry 573, no. 2 (2004): 215–25. http://dx.doi.org/10.1016/j.jelechem.2004.07.007.

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7

Apoorv, Saraswat, Kant Sharma Laxmi, and K. P. Singh R. "Electrogenerated base : A green protocol for synthesis of arylidene malononitrile." Journal of Indian Chemical Society Vol. 89, Jan 2012 (2012): 111–15. https://doi.org/10.5281/zenodo.5751781.

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Electrochemical Laboratory of Green Synthesis, Department of Chemistry, University of Allahabad, Allahabad-211 002, Uttar Pradesh, India <em>E-mail</em> : rkp.singh@rediffmail.com <em>Manuscript received 27 October 2010, revised 19 March 2011, accepted 26 May 2011</em> A simple electrochemical synthesis of arylidene malononitrile from different aldehydes are studied and discussed here. A controlled potential electrolysis was carried out in undivided cell in the presence of acetonitrile as a solvent and lithium perchlorate as a supporting electrolyte. Electrogenerated base of malononitrile reac

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8

Matsumoto, Kouichi, Yuta Hayashi, Kengo Hamasaki, et al. "Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates." Beilstein Journal of Organic Chemistry 18 (August 29, 2022): 1116–22. http://dx.doi.org/10.3762/bjoc.18.114.

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The electrochemical reduction conditions of the reaction of alkyl 2-chloroacetates in Bu4NBr/DMF using a divided cell equipped with Pt electrodes to produce the corresponding cyclopropane derivatives in moderate yields were discovered. The reaction conditions were optimized, the scope and limitations, as well as scale-up reactions were investigated. The presented method for the electrochemical production of cyclopropane derivatives is an environmentally friendly and easy to perform synthetic procedure.

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9

Li, Wei-Cui, Zheng-Zheng Zhang, Cheng-Chu Zeng, Li-Ming Hu, and Hong-Yu Tian. "Electrogenerated Base Induced Dehydrodimerization and Dehydrotrimerization of Pyrazolones." Current Organic Synthesis 11, no. 3 (2014): 454–60. http://dx.doi.org/10.2174/15701794113109990002.

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10

Fotouhi, Lida, Majid M. Heravi, Azadeh Fatehi, and Khadijeh Bakhtiari. "Electrogenerated base-promoted synthesis of tetrahydrobenzo[b]pyran derivatives." Tetrahedron Letters 48, no. 31 (2007): 5379–81. http://dx.doi.org/10.1016/j.tetlet.2007.06.035.

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11

Chiarotto, Isabella, Leonardo Mattiello, and Marta Feroci. "The Electrogenerated Cyanomethyl Anion: An Old Base Still Smart." Accounts of Chemical Research 52, no. 12 (2019): 3297–308. http://dx.doi.org/10.1021/acs.accounts.9b00465.

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12

Kashimura, S., Y. Murai, M. Ishifune, et al. "Formation of electrogenerated base by the electroreduction of polyacrylamides." Electrochimica Acta 42, no. 13-14 (1997): 2241–45. http://dx.doi.org/10.1016/s0013-4686(97)85505-3.

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13

Barhdadi, Rachid, Michel Troupel, and Jacques Périchon. "Coupling of fluoroform with aldehydes using an electrogenerated base." Chemical Communications, no. 12 (1998): 1251–52. http://dx.doi.org/10.1039/a801406j.

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14

SUCHITRA, DWIVEDI, SINGH MANORAMA, and ACHAL MISRA RAM. "Reaction of Organohalogens with in situ Electrogenerated Superoxide Ion." Journal of Indian Chemical Society Vol. 72, Jan 1995 (1995): 37–39. https://doi.org/10.5281/zenodo.5900455.

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Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221 005 <em>Manuscript received 26 May 1993, revised 4 August 1993, accepted 12 October 1993</em> Superoxide ion, generated by electrochemical reduction of 02 in dimethylformamide at mercury cathode, reacts as an effective nucleophile with haloarenes (1a-4a) and as a base with phenacyl halides (5a and 6a) affording phenols (la-4b) and <em>trans</em>-dibenzoylethene (5b) respectively.

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15

Zhu, Jing-Wei, Meng-Han Li, Feng Zhang, Ya-Li Wang, Jia-Xing Lu, and Huan Wang. "Effect of Solvents on Electrogenerated Base-Driven Transfer Hydrogenation Reactions." Molecules 30, no. 4 (2025): 910. https://doi.org/10.3390/molecules30040910.

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Transfer hydrogenation is a crucial technology for synthesizing fine chemicals and pharmaceuticals, offering improved safety and convenience over traditional hydrogen methods, although it typically requires external bases. While isopropanol is commonly used as a hydrogen source, methanol is superior but faces challenges due to its high dehydrogenation energy barrier, limiting its use under mild conditions. This study focuses on investigating the differences in the electrogenerated base-driven transfer hydrogenation of aromatic ketones in isopropanol and methanol solvents, using Mn(CO)₅Br and c

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16

Tissaoui, Khalil, Noureddine Raouafi, and Khaled Boujlel. "Electrogenerated base-promoted synthesis ofN-benzylic rhodanine and carbamodithioate derivatives." Journal of Sulfur Chemistry 31, no. 1 (2010): 41–48. http://dx.doi.org/10.1080/17415990903191752.

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17

Feroci, Marta, Achille Inesi, Laura Palombi, Leucio Rossi, and Giovanni Sotgiu. "Electrogenerated Base-Induced N-Acylation of Chiral Oxazolidin-2-ones." Journal of Organic Chemistry 66, no. 18 (2001): 6185–88. http://dx.doi.org/10.1021/jo010038+.

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18

Homma, Haruka, Ruka Hasegawa, Tomohiro Yokoyama та Toshiki Tajima. "Convergent Paired Electrosynthesis of β-Nitroalcohols Using an Electrogenerated Base". ECS Meeting Abstracts MA2024-02, № 53 (2024): 3635. https://doi.org/10.1149/ma2024-02533635mtgabs.

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Organic electrosynthesis has attracted much attention as an environmentally benign organic synthesis process, because it is a redox process that does not use oxidizing or reducing agents. In organic electrosynthesis, only one of the reactions, oxidation at the anode or reduction at the cathode, is often targeted, and the counter electrode is mostly used only to conduct electric current. In contrast, paired electrosynthesis targets both anodic and cathodic reactions and is attractive from the viewpoint of current efficiency. Furthermore, convergent paired electrosynthesis, which yields a single

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19

Sbei, Najwa, Belen Batanero, Fructuoso Barba, Beya Haouas, Mohamed Lamine Benkhoud, and Isidoro Barba. "Facile preparation of 3-substituted 2-quinazolinones via electrogenerated base." Tetrahedron 74, no. 16 (2018): 2068–72. http://dx.doi.org/10.1016/j.tet.2018.03.010.

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20

Felton, Greg A. N. "Electrocatalytic reactions: anion radical cyclobutanation reactions and electrogenerated base reactions." Tetrahedron Letters 49, no. 5 (2008): 884–87. http://dx.doi.org/10.1016/j.tetlet.2007.11.171.

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21

Tokuda, Masao, and Osamu Nishio. "Deconjugative alkylation of .alpha.,.beta.-acetylenic esters by electrogenerated base." Journal of Organic Chemistry 50, no. 10 (1985): 1592–96. http://dx.doi.org/10.1021/jo00210a006.

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22

Gard, J. C., B. Hanquet, L. Roullier, Y. Mugnier, and J. Lessard. "Electrochemically induced chain reactions: the addition of fluorene and indene to aromatic aldehydes initiated by electrochemical reduction." Canadian Journal of Chemistry 74, no. 1 (1996): 55–63. http://dx.doi.org/10.1139/v96-007.

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The electrochemical reduction at −30 °C of 2,6-dichlorobenzaldehyde (1a), benzaldehyde (1b), and terephthalaldehyde (2) in tetrahydrofuran with tetrabutylammonium perchlorate as supporting electrolyte, under an argon atmosphere and in the presence of fluorene or indene, gives carbinols resulting from the addition of fluorene or indene and requires only a catalytic amount of electricity. The chain reaction is initiated by proton abstraction from fluorene or indene by a base electrogenerated by reduction of the aldehyde and the propagation involves the addition of the carbanion to the aldehyde f

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23

Torii, Sigeru, Yasuo Murakami, Hideo Tanaka, and Koichi Okamoto. "Electrogenerated base (EG Base) induced hydroxymethylation of the side chain of nitroalkylbenzenes with paraformaldehyde." Journal of Organic Chemistry 51, no. 16 (1986): 3143–47. http://dx.doi.org/10.1021/jo00366a012.

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24

Kimura, Makoto, Hiroyoshi Miyahara, Noriyuki Moritani, and Yasuhiko Sawaki. "Electroreductive dehalogenation of chlorinated aromatic ethers. Unexpected electrogenerated base-catalyzed reactions." Journal of Organic Chemistry 55, no. 12 (1990): 3897–902. http://dx.doi.org/10.1021/jo00299a037.

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25

Feroci, Marta, Achille Inesi, Laura Palombi, and Giovanni Sotgiu. "Electrogenerated Base-Induced N-Acylation of Chiral Oxazolidin-2-ones. 21." Journal of Organic Chemistry 67, no. 5 (2002): 1719–21. http://dx.doi.org/10.1021/jo016323a.

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26

BARHDADI, R., M. TROUPEL, and J. PERICHON. "ChemInform Abstract: Coupling of Fluoroform with Aldehydes Using an Electrogenerated Base." ChemInform 29, no. 42 (2010): no. http://dx.doi.org/10.1002/chin.199842091.

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27

Fuchigami, Toshio, Kaoru Suzuki, and Tsutomu Nonaka. "Electrogenerated triphenylmethyl anion species—a highly useful base for selective organic synthesis." Electrochimica Acta 35, no. 1 (1990): 239–44. http://dx.doi.org/10.1016/0013-4686(90)85064-t.

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28

Feroci, Marta, Achille Inesi, Laura Palombi, Leucio Rossi, and Giovanni Sotgiu. "ChemInform Abstract: Electrogenerated Base-Induced N-Acylation of Chiral Oxazolidin-2-ones." ChemInform 33, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.200203072.

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29

Saraswat, Apoorv, Laxmi Kant Sharma, and R. K. P. Singh. "ChemInform Abstract: Electrogenerated Base: A Green Protocol for Synthesis of Arylidene Malononitrile." ChemInform 43, no. 46 (2012): no. http://dx.doi.org/10.1002/chin.201246081.

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30

Casadei, Maria Antonietta, Stefania Cesa, and Leucio Rossi. "Electrogenerated Base-Promoted Synthesis of Organic Carbonates from Alcohols and Carbon Dioxide." European Journal of Organic Chemistry 2000, no. 13 (2000): 2445–48. http://dx.doi.org/10.1002/1099-0690(200007)2000:13<2445::aid-ejoc2445>3.0.co;2-2.

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31

Torii, Sigeru, Hiroshi Okumoto, Taro Kiyoto, and Shigeki Hikasa. "A Facile Hydroxymethylation of Acetylene Derivatives with Paraformaldehyde by Use of an Electrogenerated Base (EG Base)." Chemistry Letters 17, no. 12 (1988): 1977–78. http://dx.doi.org/10.1246/cl.1988.1977.

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32

Saied, Taieb, Noureddine Raouafi, and Khaled Boujlel. "An Electrogenerated Base-Promoted Synthesis of 2-Aryl-3,3-Bis((Perfluoroalkyl) Thio)Acrylonitriles." Phosphorus, Sulfur, and Silicon and the Related Elements 188, no. 10 (2013): 1320–26. http://dx.doi.org/10.1080/10426507.2013.765872.

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33

Bonafoux, Dominique, Michel Bordeau, Claude Biran, and Jacques Dunoguès. "Regioselective Synthesis of 2,2-Dimethylcyclopentanone Using 2-Pyrrolidone Magnesium Salt as Electrogenerated Base." Synthetic Communications 28, no. 1 (1998): 93–98. http://dx.doi.org/10.1080/00397919808005077.

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34

Feroci, Marta, Achille Inesi, and Leucio Rossi. "The reaction of amines with an electrogenerated base. Improved synthesis of arylcarbamic esters." Tetrahedron Letters 41, no. 6 (2000): 963–66. http://dx.doi.org/10.1016/s0040-4039(99)02180-2.

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35

Kimura, Makoto, Tsutomu Yamashita, Tsunehiko Kurata, and Yasuhiko Sawaki. "Water as an effective precursor of electrogenerated base. Facile alkylation of dialkyl phosphonates." Journal of the Chemical Society, Chemical Communications, no. 3 (1990): 259. http://dx.doi.org/10.1039/c39900000259.

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36

Feroci, Marta, Martina Bortolami, Isabella Chiarotto, et al. "An Insight into the Reactivity of the Electrogenerated Radical Cation of Caffeine." Electrochem 1, no. 1 (2020): 44–55. http://dx.doi.org/10.3390/electrochem1010005.

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Controlled potential electrolyses of caffeine (CAF) were carried out at a Pt electrode in undried acetonitrile (ACN) and ACN-H2O and the products of the anodic oxidation were analyzed by HPLC-PDA-ESI-MS/MS. A higher current efficiency occurred in ACN-H2O, but an analogous chromatographic outline was found in both media, evidencing a reactive pathway of the electrogenerated radical cation CAF•+ with water, added or in trace, as nucleophile. No dimeric forms were evidenced, excluding any coupling reactions. Neither was 1,3,7-trimethyluric acid found, reported in the literature as the main oxidat

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37

Feroci, Marta, Isabella Chiarotto, Gianpiero Forte, et al. "Efficient Electrochemical N-Alkylation of N-Boc-Protected 4-Aminopyridines: Towards New Biologically Active Compounds." ISRN Organic Chemistry 2014 (March 5, 2014): 1–10. http://dx.doi.org/10.1155/2014/621592.

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The use of electrogenerated acetonitrile anion allows the alkylation of N-Boc-4-aminopyridine in very high yields, under mild conditions and without by-products. The high reactivity of this base is due to its large tetraethylammonium counterion, which leaves the acetonitrile anion “naked.” The deprotection of the obtained compounds led to high yields in N-alkylated 4-aminopyridines. Nonsymmetrically dialkylated 4-aminopyridines were obtained by subsequent reaction of monoalkylated ones with t-BuOK and alkyl halides, while symmetrically dialkylated 4-aminopyridines were obtained by direct react

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38

Li, Shuhuai, Chunhua Liu, Guihao Yin, Qun Zhang, Jinhui Luo, and Nanchun Wu. "Aptamer-molecularly imprinted sensor base on electrogenerated chemiluminescence energy transfer for detection of lincomycin." Biosensors and Bioelectronics 91 (May 2017): 687–91. http://dx.doi.org/10.1016/j.bios.2017.01.038.

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39

Feroci, Marta, Achille Inesi, Laura Palombi, and Giovanni Sotgiu. "ChemInform Abstract: Electrogenerated Base-Induced N-Acylation of Chiral Oxazolidin-2-ones. Part 2." ChemInform 33, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.200233071.

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40

Lay, PA, AF Masters, and CD Wasiowych. "The Reactions of Electrogenerated [Ni(sacsac)2]-: Biomimetic Chemistry Related to Nickel Enzymes." Australian Journal of Chemistry 48, no. 4 (1995): 835. http://dx.doi.org/10.1071/ch9950835.

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The electrochemical reduction of [Ni( sacsac )2] ( sacsac = C5H7S2- = pentane-2,4-dithionate) has been investigated by cyclic voltammetry and controlled-potential electrolysis in acetone/tetra- butylammonium tetrafluoroborate (0.1 M). The reactions of the reduction product(s) with CO, CO2, CH3I, C12H25SH, light and water have been surveyed. At a scan rate of 100 mV s-1, [Ni( sacsac )2] (0.5 mM ) undergoes a quasi-reversible one-electron reduction (∆ Ep = 88 mV) at -1.543 V (v. Fc+/0) and an irreversible four-electron oxidation at +0.635 V. The oxidation generates the 3,5-dimethyl-1,2-dithioliu

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41

Haouas, Beya, Taieb Saied, Hanen Ayari, Youssef Arfaoui, Mohamed Lamine Benkhoud, and Khaled Boujlel. "Electrogenerated base-promoted synthesis and antimicrobial activity of 2-imino-1,3-thiazolidin-4-one derivatives." Journal of Sulfur Chemistry 37, no. 4 (2016): 391–400. http://dx.doi.org/10.1080/17415993.2016.1155588.

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42

Torii, Sigeru, Hiroyuki Kawafuchi, and Tsutomu Inokuchi. "An Improved Cyanoalkylation Method of Aldehydes Catalyzed by Electrogenerated Base in a DMF–H2O System." Bulletin of the Chemical Society of Japan 63, no. 8 (1990): 2430–32. http://dx.doi.org/10.1246/bcsj.63.2430.

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43

Bonafoux, Dominique, Michel Bordeau, Claude Biran, Philippe Cazeau, and Jacques Dunogues. "Regio- and Stereoselective Synthesis of Silyl Enol Ethers Using a New Base Electrogenerated from Hexamethyldisilazane." Journal of Organic Chemistry 61, no. 16 (1996): 5532–36. http://dx.doi.org/10.1021/jo960493j.

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44

Shono, Tatsuya, Manabu Ishifune, Toshio Okada, and Shigenori Kashimura. "Electroorganic chemistry. 130. A novel trifluoromethylation of aldehydes and ketones promoted by an electrogenerated base." Journal of Organic Chemistry 56, no. 1 (1991): 2–4. http://dx.doi.org/10.1021/jo00001a002.

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45

Feroci, Marta, Achille Inesi, and Leucio Rossi. "ChemInform Abstract: The Reaction of Amines with an Electrogenerated Base. Improved Synthesis of Arylcarbamic Esters." ChemInform 31, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.200016093.

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46

BONAFOUX, D., M. BORDEAU, C. BIRAN, and J. DUNOGUES. "ChemInform Abstract: Regioselective Synthesis of 2,2-Dimethylcyclopentanone Using 2-Pyrrolidone Magnesium Salt as Electrogenerated Base." ChemInform 29, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199820108.

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47

Dzudovic, Radmila, and Ljiljana Jaksic. "Coulometric-potentiometric determination of autoprotolysis constant and relative acidity scale of water." Journal of the Serbian Chemical Society 75, no. 11 (2010): 1575–82. http://dx.doi.org/10.2298/jsc100316094d.

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The autoprotolysis constant and relative acidity scale of water were determined by applying the coulometric-potentiometric method and a hydrogen/palladium (H2/Pd) generator anode. In the described procedure for the evaluation of autoprotolysis constant, a strong base generated coulometrically at the platinum cathode in situ in the electrolytic cell, in presence of sodium perchlorate as the supporting electrolyte, is titrated with hydrogen ions obtained by the anodic oxidation of hydrogen dissolved in palladium electrode. The titration was carried out with a glass-SCE electrode pair at 25.0?0.1

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48

Tissaoui, Khalil, Noureddine Raouafi, and Khaled Boujlel. "Electrogenerated base promoted synthesis of N-substituted-4-hydroxy-4-methylthiazolidine-2-thione derivatives." Journal of Chemical Research 2009, no. 11 (2009): 710–12. http://dx.doi.org/10.3184/030823409x12572506562749.

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49

Freire, Cristina, and Baltazar de Castro. "Spectroscopic characterisation of electrogenerated nickel(III) species. Complexes with N2O2 Schiff-base ligands derived from salicylaldehyde." Journal of the Chemical Society, Dalton Transactions, no. 9 (1998): 1491–98. http://dx.doi.org/10.1039/a708231b.

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50

Sbei, Najwa, Belen Batanero, Fructuoso Barba, Beya Haouas, Luis Fuentes, and Mohamed Lamine Benkhoud. "A convenient synthesis of new biological active 5-imino-4-thioxo-2-imidazolidinones involving acetonitrile electrogenerated base." Tetrahedron 71, no. 40 (2015): 7654–57. http://dx.doi.org/10.1016/j.tet.2015.07.066.

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