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

• have shown that the choice of solvent significantly impacts the reaction. CH₃CN exhibits better than CH₃OH, with a wider electrochemical window and better reactant solubility. When the reaction was conducted in CH₃CN using n-Bu₄NPF₆ and n-Bu₄NBF₄ as electrolytes but without iodide salt and in the

• were obtained using platinum electrodes as the anode and cathode (Scheme 25). Studies showed that CH₃CN performed better than CH₃OH due to its wider electrochemical window and better solubility. The results indicated that the electronic properties of substituents had no significant effect on the yield

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• reverse CV branch of 9, characteristic of compounds with a catechol fragment (Figure S24 in Supporting Information File 1). The second anodic peak for 9 is not observed due to the narrow electrochemical window of the solvent in the positive CV region. The formation of o-benzoquinones at the first stage of

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

• −1.2V to −1.3 V region (Table 1). In case of S2, the second reduction peak corresponds to the reduction of the carbonyl group. Thus, the electrochemical window for the new salts exceeds 3.5 V; that makes their molten forms perspective for application as ionic liquids. As follows from Table 1, oxidation

Synthesis and physical properties of tunable aryl alkyl ionic liquids based on 1-aryl-4,5-dimethylimidazolium cations

• Stefan Fritsch and
• Thomas Strassner

Beilstein J. Org. Chem. 2024, 20, 1278–1285, doi:10.3762/bjoc.20.110

• -donating substituents in different positions of the phenyl ring and the bis(trifluoromethylsulfonyl)imide (NTf2) anion. We investigated the effect of additional methyl groups in the backbone of the imidazolium core on the physical properties regarding viscosity, conductivity and electrochemical window

• . With an electrochemical window of up to 6.3 V, which is unprecedented for TAAILs with an NTf2 anion, this new class of TAAILs demonstrates the opportunities that arise from modifications in the backbone of the imidazolium cation. Keywords: conductivity; electrochemical window; ionic liquids; tunable

• and para position of the substituent on the properties of the IL. For the [NTf2]− salts of the TAAILs, the viscosity, conductivity and the electrochemical window were determined. Results and Discussion In this work we focused on a synthetic strategy with cost efficient starting materials and a good

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

• [90][91]. Due to their wide electrochemical window, imidazolium ILs are commonly used in organic electrochemistry, simultaneously as solvents and supporting electrolytes [92][93][94]. In addition, the cathodic reduction (both in batch [95] and in flow [96]) can be exploited for the generation of N

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• derivatives 6–9. Their 5% weight loss temperatures (Td) ranged from 433 to 493 °C (Figure 5a and Table 1). Electrochemical properties The electrochemical properties of compounds 6–9 were studied by cyclic voltammetry (CV) selecting the electrochemical window from −1.6 to 1.7 V and the CV data were corrected

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

• recycle them, good stability, low flammability, good solubility ability for many molecules, salts and gases, the possibility to use them as reagents and/or solvents, large electrochemical window, good electrical conductivity, their ionic nature sometimes increases the reactivity and the selectivity of

Enhanced quantum yields by sterically demanding aryl-substituted β-diketonate ancillary ligands

• Rebecca Pittkowski and
• Thomas Strassner

Beilstein J. Org. Chem. 2018, 14, 664–671, doi:10.3762/bjoc.14.54

• V vs ferrocene for both complexes. No reduction was observed for both complexes in the electrochemical window of the solvent. Thus, the electrochemical behavior of the newly synthesized substances is comparable. Discussion Compared to the already published, structurally related 3-methyl-1

Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone

• Ernesto Emmanuel López-López,
• José Alvano Pérez-Bautista,
• Fernando Sartillo-Piscil and
• Bernardo A. Frontana-Uribe

Beilstein J. Org. Chem. 2018, 14, 547–552, doi:10.3762/bjoc.14.41

• derivatives [32][33], showing a convenient electrochemical window with graphitic electrodes (−1.75 to 1.25 V vs Ag/AgCl) and giving good environmental compatibility. Cyclic voltammetry of thiocarbonates 4 and 6 using a vitreous carbon electrode, showed two irreversible reduction peaks located at −1.18 and

Electrosynthesis and electrochemistry

• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 949–950, doi:10.3762/bjoc.11.105

• ]. In addition, remarkable breakthroughs have been achieved regarding electrodes and electrolytes, which allow for expansion of the electrochemical window and/or novel reaction pathways. This leads to new electro-organic concepts and further applications for a sustainable synthetic methodology. The

IR and electrochemical synthesis and characterization of thin films of PEDOT grown on platinum single crystal electrodes in [EMMIM]Tf₂N ionic liquid

• Andrea P. Sandoval,
• Marco F. Suárez-Herrera and
• Juan M. Feliu

Beilstein J. Org. Chem. 2015, 11, 348–357, doi:10.3762/bjoc.11.40

• ) has shown an enhancement in stability, organization and electroactivity [12][13][14]. These characteristics are obtained mainly because of the dry medium, their wide electrochemical window, and their low nucleophilicity. Therefore, during the electrosynthesis of conducting polymers the overoxidation

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• ]. Their negligible vapor pressure, large electrochemical window, good intrinsic conductivity and high CO2 solubility make them interesting solvents for electrochemical CO2 valorization [81][82][83][99][100][101]. Under similar conditions, ketones are carboxylated with higher selectivity for the α-hydroxy

Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

• Irina P. Romanova,
• Andrei V. Bogdanov,
• Inessa A. Izdelieva,
• Vasily A. Trukhanov,
• Gulnara R. Shaikhutdinova,
• Dmitry G. Yakhvarov,
• Shamil K. Latypov,
• Vladimir F. Mironov,
• Vladimir A. Dyakov,
• Ilya V. Golovnin,
• Dmitry Yu. Paraschuk and
• Oleg G. Sinyashin

Beilstein J. Org. Chem. 2014, 10, 1121–1128, doi:10.3762/bjoc.10.111

• peaks are observed in the CV data of AMF 1–9. Table 1 summarizes the results, and Figure 3 presents a typical CV curve of AIM. Note that both the fullerene sphere and the indolinone fragment are electrochemically active in the working electrochemical window. Thus, the pristine fullerene C60 and isatins

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

• Filipe Vilela,
• Peter J. Skabara,
• Christopher R. Mason,
• Thomas D. J. Westgate,
• Asun Luquin,
• Simon J. Coles and
• Michael B. Hursthouse

Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113

• redox processes are collated in Table 1. In compounds 3 and 27 an irreversible single electron oxidation wave is seen at +1170 mV and +900 mV, respectively. Further oxidation processes of these materials do not occur within the electrochemical window of the solvent. The electron withdrawing effect of

• of the TTF dication hinders subsequent removal of an electron from the thiophene units, so further oxidations are beyond the electrochemical window of the solvent. Compound 28 is reversibly oxidised to 28+· at −740 mV, within the range seen in other nickel dithiolene complexes. A second single

A convenient method for preparing rigid-core ionic liquid crystals

• Julien Fouchet,
• Laurent Douce,
• Benoît Heinrich,
• Richard Welter and
• Alain Louati

Beilstein J. Org. Chem. 2009, 5, No. 51, doi:10.3762/bjoc.5.51

• liquids (ILs) have revealed their many useful properties such as extremely low volatility, high thermal stability, non-flammability, high chemical and radiochemical stability, high ionic conductivity and wide electrochemical window [1][2][3]. In addition, the ILs have been used as reaction media