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Search for "electrochemical synthesis" in Full Text gives 36 result(s) in Beilstein Journal of Organic Chemistry.

Recent advances in the electrochemical synthesis of organophosphorus compounds

  • Babak Kaboudin,
  • Milad Behroozi,
  • Sepideh Sadighi and
  • Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

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  • used extensively for the electrochemical synthesis of organophosphorus compounds. The recent advances in the electrochemical synthesis of organophosphorus compounds have made this method a promising method for preparing various structures. This review is an introduction to encourage scientists to use
  • electrosynthesis as a green, precise, and low-cost method to prepare phosphorous structures. Keywords: electrosynthesis; green synthesis; organophosphorus compounds; P–C bond formation; P–heteroatom bond formation; Introduction The electrochemical synthesis is a valuable and beneficial method for the preparation
  • “greener chemistry”. Today, electrochemical synthesis has many applications in industry, and thousands of tons of chemicals are produced by this method every year [1][2][3][4][5][6][7][8][9][10][11]. In electrochemical synthesis, only electricity is used instead of oxidizing or reducing substances
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Published 16 Apr 2025

Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters

  • Olesja Koleda,
  • Janis Sadauskis,
  • Darja Antonenko,
  • Edvards Janis Treijs,
  • Raivis Davis Steberis and
  • Edgars Suna

Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50

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  • 10.3762/bjoc.21.50 Abstract The electrochemical synthesis of 2-aminoprolines based on anodic decarboxylation–intramolecular amidation of readily available N-acetylamino malonic acid monoesters is reported. The decarboxylative amidation under Hofer–Moest reaction conditions proceeds in an undivided cell
  • and the development of efficient synthetic methods to access these medicinally relevant structural motifs. Herein, we report an electrochemical synthesis of 2-aminoproline and 2-aminopipecolic acid derivatives 6 (Figure 1). Recently, we disclosed an electrochemical approach to tetrahydrofuran and
  • electrochemical synthesis of pyrrolidines 6a–f,j–n from the corresponding malonic acid monoesters 9a–f,j–n. An undivided electrochemical cell (5 mL, IKA ElectraSyn 2.0) was charged with starting carboxylic acid 9a–f,j–n (0.2–0.3 mmol) and Et4N–BF4 (0.025 M), followed by addition of MeCN (2.5 mL) and H2O (0.5 mL
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Published 19 Mar 2025

Electrochemical synthesis of cyclic biaryl λ3-bromanes from 2,2’-dibromobiphenyls

  • Andrejs Savkins and
  • Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

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  • an electrochemical synthesis of cyclic diaryl λ3-bromanes under anodic oxidation conditions. Results and Discussion Symmetric 2,2'-dibromo-1,1'-biphenyl 4a possessing ethoxycarbonyl groups ortho to the bromine was chosen as a model compound for our study. We anticipated that the presence of the ester
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Published 27 Feb 2025

Hypervalent iodine-mediated intramolecular alkene halocyclisation

  • Charu Bansal,
  • Oliver Ruggles,
  • Albert C. Rowett and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

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  • fluoroacetate as an internal standard). Electrochemical synthesis of fluorinated oxazolines. Electrochemical synthesis of chromanes. Synthesis of fluorinated oxazepanes. Enantioselective oxy-fluorination with a chiral aryliodide catayst. Catalytic synthesis of 5‑fluoro-2-aryloxazolines using BF3·Et2O as a
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Published 28 Nov 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

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Published 09 Oct 2024

Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

  • Hisanori Senboku and
  • Mizuki Hayama

Beilstein J. Org. Chem. 2024, 20, 2392–2400, doi:10.3762/bjoc.20.203

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  • electrochemical method. Instead of DMF and acetonitrile, which have frequently been used for electrochemical carboxylation, DMSO was found to be effective for electrochemical carboxylation of diarylmethanol compounds 1 in order to provide diarylacetic acids 2. The present electrochemical synthesis is promising as
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Published 20 Sep 2024

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

  • Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

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  • employed ferrocene as electrocatalyst instead of iodide salts. Additionally, Tang et al. demonstrated that amidines could react with preformed aldehydes-derived hydrazones to produce similar 1,3,5-trisubstituted 1,2,4-triazoles [54]. The last example of electrochemical synthesis of trisubstituted 1,2,4
  • electrochemical synthesis of diazo compounds from hydrazones. Transformations involving diazo compounds as either products or intermediates are covered. While investigating the electrochemical oxidation of benzophenone hydrazones 130, Chiba et al. discovered that several products were obtained depending on the
  • point of view, the authors proposed the formation of N-pyridyl radical 18 through the anodic oxidation of in situ-generated anion 17. Subsequent radical cyclization, second anodic cyclization and deprotonation yielded the fused heterocycle 16. Similarly, Youssef and Alajimi disclosed the electrochemical
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Published 14 Aug 2024

Novel oxidative routes to N-arylpyridoindazolium salts

  • Oleg A. Levitskiy,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

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  • -pyridine substituted diarylamines, either using bis(trifluoroacetoxy)iodobenzene as an oxidant, or electrochemically, via potentiostatic oxidation. Electrochemical synthesis occurs under mild conditions; no chemical reagents are required except electric current. Both approaches can be considered as a late
  • amine oxidation is increased. Electrochemical synthesis of pyridoindazolium salts The results of the voltammetry testing allowed to assume that pyridoindazolium salts can also be obtained using an anodic synthesis. Electric current as a reagent is inherently safe and easily scalable; electrosynthesis is
  • the ortho-pyridine-substituted diarylamines. The oxidation can be performed either chemically, using bis(trifluoroacetoxy)iodobenzene as the oxidant, or electrochemically, via potentiostatic oxidation. The electrochemical synthesis occurs under mild conditions; no chemical reagents are required except
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Published 07 Aug 2024

Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)

  • Hiwot M. Tiruye,
  • Solon Economopoulos and
  • Kåre B. Jørgensen

Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153

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  • making them less desirable for industrial scale [19]. Electrochemical synthesis methods have a huge potential and this field is currently undergoing a renaissance [20][21][22][23][24]. Replacing chemical oxidants with electric current reduces waste production and gives a sustainable and inherently safe
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Published 24 Jul 2024

1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF3: the case of alkyne hydration. Chemistry vs electrochemistry

  • Marta David,
  • Elisa Galli,
  • Richard C. D. Brown,
  • Marta Feroci,
  • Fabrizio Vetica and
  • Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

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  • the aldol condensation products. Importantly, the ability to recycle the ionic liquid in subsequent reactions was successfully demonstrated. Keywords: alkyne hydration; boron trifluoride; electrochemical synthesis; ionic liquids; Introduction Alkynes are fundamental starting materials towards more
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Published 28 Dec 2023

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

  • Elena R. Lopat’eva,
  • Igor B. Krylov,
  • Dmitry A. Lapshin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

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  • oxidative organocatalysis. Electrochemical DDQ-catalyzed intramolecular dehydrogenative aryl–aryl coupling. DDQ-mediated cross-dehydrogenative C–N coupling of benzylic substrates with azoles. Biomimetic o-quinone-catalyzed benzylic alcohol oxidation. Electrochemical synthesis of secondary amines by
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Published 09 Dec 2022

Molecular and macromolecular electrochemistry: synthesis, mechanism, and redox properties

  • Shinsuke Inagi and
  • Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 1505–1506, doi:10.3762/bjoc.18.158

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  • reactions to produce value-added products. Electrochemical synthesis (or simply electrosynthesis) is increasingly recognized for the high academic and industrial importance, in line with the concept of green chemistry proposed in 1998 and the Sustainable Development Goals (SDGs) adopted by the United
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Editorial
Published 26 Oct 2022

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

  • Shang-Feng Yang,
  • Pei Li,
  • Zi-Lin Fang,
  • Sen Liang,
  • Hong-Yu Tian,
  • Bao-Guo Sun,
  • Kun Xu and
  • Cheng-Chu Zeng

Beilstein J. Org. Chem. 2022, 18, 1249–1255, doi:10.3762/bjoc.18.130

Graphical Abstract
  • -alanine-assisted one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I (Scheme 1d). This electrochemical method features external-oxidant-free conditions and avoids the prefunctionalization of the substrates. Results and Discussion To
  • dehydration to give the heterocyclic product 3. At the cathode, protons are reduced to release H2. Conclusion In conclusion, we have developed a one-pot electrochemical strategy for the synthesis of 2-amniothiazoles by the reaction of active methylene ketones with thioureas. The electrochemical synthesis was
  • mmol) in DMSO 1 mL + H2O 14 mL, undivided cell, graphite plate anode and cathode, 30 °C, 5 mA/cm2, 6 F/mol; isolated yields are given. a8 F/mol. Up-scaling experiment. Control experiments. The proposed mechanism for the one-pot electrochemical synthesis of 2-aminothiazoles mediated by NH4I
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Published 15 Sep 2022

Electrochemical formal homocoupling of sec-alcohols

  • Kosuke Yamamoto,
  • Kazuhisa Arita,
  • Masashi Shiota,
  • Masami Kuriyama and
  • Osamu Onomura

Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

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  • formal homocoupling of benzhydrol did not occur under Kim’s reaction conditions. Thus, the development of an environmentally benign and efficient electrochemical protocol to access vic-1,2-diols would be still highly desirable. Herein, we report the sacrificial anode-free electrochemical synthesis of vic
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Published 22 Aug 2022

Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

  • Hisanori Senboku,
  • Mizuki Hayama and
  • Hidetoshi Matsuno

Beilstein J. Org. Chem. 2022, 18, 1040–1046, doi:10.3762/bjoc.18.105

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  • was carried out using Et3NHBF4 at −10 °C (Table 2, entry 3). Instead of Et3NHBF4, sterically more hindered iPr2NHEtBF4 was effective for the electrochemical synthesis to give the desired compound 2 in the highest yield, 72% by 1H NMR (Table 2, entry 4). These results strongly indicate that
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Published 18 Aug 2022

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

  • Daniele Rocco,
  • Ana A. Folgueiras-Amador,
  • Richard C. D. Brown and
  • Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

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  • methanol and the Breslow intermediate. Electrochemical reduction of BMImBF4,a followed by the addition of elemental sulfurb. Flow cell, in recycling mode. Electrochemical synthesis of γ-butyrolactones 2a and 2b by conjugate umpolung reaction.a Electrochemical synthesis of esters 3a–c from cinnamaldehyde
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Published 05 Aug 2022

Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications

  • Sadanobu Iwase,
  • Shinsuke Inagi and
  • Toshio Fuchigami

Beilstein J. Org. Chem. 2022, 18, 872–880, doi:10.3762/bjoc.18.88

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  • , these methods require various metal and organometallic reagents. On the other hand, electrochemical organic synthesis is a metal-free process and does not require any hazardous reagents and it produces less waste than conventional chemical syntheses. Therefore, electrochemical synthesis is desirable
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Published 20 Jul 2022

Menadione: a platform and a target to valuable compounds synthesis

  • Acácio S. de Souza,
  • Ruan Carlos B. Ribeiro,
  • Dora C. S. Costa,
  • Fernanda P. Pauli,
  • David R. Pinho,
  • Matheus G. de Moraes,
  • Fernando de C. da Silva,
  • Luana da S. M. Forezi and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

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  • -methyl-1,4-dimethoxynaphthalene, the construction of the naphthoquinone ring, the methylation of 1,4-naphthoquinone, and the electrochemical synthesis from 2-methyl-1,4-dihydroxynaphthalene. The works discussed in this section are grouped according to the synthetic approach that was employed to prepare
  • catalyst, in the presence of 1,3-butadiene, presented the best yield (about 33%) (Scheme 9). This presented itself as a good synthetic route, considering that it used easily accessible reagents and there was no formation of polluting products. Electrochemical synthesis Although not common, menadione (10
  • ) can be readily produced through electrochemical synthesis. This methodology allows the reuse of the electrolyte and demonstrates a significant substrate conversion. Raju and co-workers [94], for instance, reported the electrochemical synthesis of 10 from menadiol (14) using galvanostatic biphasic
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Published 11 Apr 2022

Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

  • Yuki Naito,
  • Naoki Shida and
  • Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

Graphical Abstract
  • . Furthermore, piperidine and pyrrolidine derivatives could be obtained on preparative scale by continuous electrolysis for approximately 1 hour. Keywords: electrochemical synthesis; electrocyclization; flow microreactor; heterocyclic amines; imine; Introduction Heterocycles are a very important class of
  • and sustainable synthetic method in the face of increasingly stringent environmental and economic constraints. In this context, several groups have demonstrated the electrochemical synthesis of piperidine and pyrrolidine derivatives by anodic oxidation [22][23][24][25][26]. In contrast, there has been
  • their demonstration. Therefore, it is desirable to conduct the reductive cyclizations without the use of a mercury cathode, and the development of a simple, green, and efficient method for the electrochemical synthesis of heterocyclic amines is an important research target. The electrochemical flow
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Published 29 Mar 2022

Electrocatalytic C(sp3)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis

  • Bin Guo and
  • Hai-Chao Xu

Beilstein J. Org. Chem. 2021, 17, 2650–2656, doi:10.3762/bjoc.17.178

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  • alkyne 22 afforded 1.05 g (61%) of product 14 in 13 h (Scheme 3). The productivity could be increased if multiple reactors were employed in parallel [43]. A mechanism for the electrochemical synthesis was proposed based on reported studies (Scheme 4) [3][10]. Anodic oxidation of TEMPO generates the
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Published 28 Oct 2021

Chemical syntheses and salient features of azulene-containing homo- and copolymers

  • Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

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  • synthesis in comparison to the electrochemical synthesis can be advantageous in obtaining desired patterns of substitution. Hence, this review article presents a comprehensive overview of the developments that have taken place in the last three decades in the field of chemical syntheses of azulene
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Published 24 Aug 2021

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

  • Munmun Ghosh,
  • Valmik S. Shinde and
  • Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

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  • exploiting electroorganic reactions to their fullest extent [15]. Asymmetric electrochemical synthesis refers to electroorganic reactions resulting in the introduction of one or more new elements of chirality into a target compound. The induction of asymmetry into achiral substrates through electrochemical
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Published 13 Nov 2019

A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade

  • Hong Yan,
  • Zhong-Yi Mao,
  • Zhong-Wei Hou,
  • Jinshuai Song and
  • Hai-Chao Xu

Beilstein J. Org. Chem. 2019, 15, 795–800, doi:10.3762/bjoc.15.76

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  • ] have studied the reactions of electrochemically generated NCRs. Particularly, we have recently reported an electrochemical synthesis of imidazo-fused N-heteroaromatic compounds via a radical cyclization cascade [31]. Building on this work, we report herein an atroposelective synthesis of
  • reaction. A mechanism for the electrochemical synthesis was proposed based on the results from our previous work [31] and of this work (Scheme 3). The redox catalyst 1 is oxidized at the anode to give radical cation I. In the meanwhile, H2O is reduced at the cathode to afford HO− and H2. The base generated
  • electrochemical synthesis of axially chiral biaryls. Reaction conditions: undivided cell, 2 (0.3 mmol), H2O (1 mL), MeCN (9 mL), 3.5 F mol−1. aIsolated yield of the major diastereomer. bDetermined by 1H NMR analysis of crude reaction mixture. cCombined yield of the two diastereomers. Proposed reaction mechanism
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Published 28 Mar 2019

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Mikhail A. Syroeshkin,
  • Alexander A. Korlyukov,
  • Pavel V. Dorovatovskii,
  • Yan V. Zubavichus,
  • Gennady I. Nikishin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

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  • electrochemical synthesis [2], and as mediators of living polymerization [10][11]. In organic synthesis more stable types of N-oxyl radicals can be used as carbon-centered radical scavengers [12], oxidation catalysts, mainly for conversion of alcohols to carbonyl compounds [11][13][14][15][16][17]. Less stable
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Published 16 Aug 2018

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

  • Fabiana Pandolfi,
  • Isabella Chiarotto and
  • Marta Feroci

Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76

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  • = 25 °C; solvent left: DMF/Et4NBF4 0.1 mol dm−3; right: ACN/Et4NBF4 0.1 mol dm−3. Variation of the amounts of 1a, 2a, and 3a with the number of Faradays of 1a. The Corey–Fuchs reaction. Electrochemical reduction of a carbon–halogen bond. Electrochemical synthesis of vinyl bromides [25]. Scope of this
  • . Electrochemical synthesis of 9-ethyl-3-ethynyl-9H-carbazole (2b). Electrochemical synthesis of 1-ethynyl-4-methoxybenzene (2c). Electrochemical synthesis of 2-ethynylnaphthalene (2a). Electrolysis conditions optimization (Scheme 5).a Supporting Information Supporting Information File 58: Detailed experimental
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Published 23 Apr 2018
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