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

• phosphonates for synthesizing phosphoramidates. The reaction was carried out in an undivided cell at a constant current of 10 mA using platinum electrodes as the anode and cathode and potassium iodide as a key additive. Studies have shown that the choice of solvent significantly impacts the reaction. Studies

• electrosynthesis report, Gao et al. [55] reported similar P–N coupling reactions of indoles with trialkyl phosphites in the presence of potassium iodide as a mediator and electrolyte. The carbon and platinum electrodes were used as the anode and cathode at a constant current of 5 mA for 6 h in acetonitrile as

• solvent. The results showed that potassium iodide is critical in this reaction, and the reaction failed to give a corresponding product without using KI. This reaction was quickly extended to a wide range of substituted indoles. Moreover, despite significant steric hindrance or the presence of a long

Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA

• Raphael Bereiter and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56

• nucleophilic aromatic substitution of 4-fluorobenzaldehyde with 2-(methylamino)ethanol, 3-methylamino-1-propanol or 2-[2-(methylamino)ethoxy]ethan-1-ol in the presence of potassium carbonate to afford benzaldehyde derivatives 1, 2, and 3 in excellent yields. Next, the piperidine-induced condensation with 4

• containing potassium and magnesium ions at a physiological pH of 7.0 for 5 hours. Analysis of the reaction mixture by anion-exchange HPLC revealed that the bromopropyl handle (C3 homolog 8) gave the highest yield of covalently tethered HBC-RNA complex (50%). Significantly less RNA alkylation yield was

• Exactive Orbitrap. General procedure A. 4-Fluorobenzaldehyde, the corresponding N-methylated amino alcohol and potassium carbonate were suspended in dimethyl sulfoxide and stirred for 30 hours at 120 °C. The resulting suspension was poured on crushed ice and extracted four times with chloroform, dried over

Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

• Xiao-Yang Bi,
• Xiao-Shuai Yang,
• Shan-Shan Chen,
• Jia-Jun Sui,
• Zhao-Nan Cai,
• Yong-Ming Chuan and
• Hong-Bo Qin

Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47

• DIPEA, affording compound 17 with an 89% yield [11]. For the following alkylation step with tert-butyl bromoacetate, three bases were tested: potassium carbonate, cesium carbonate, and sodium hydride. Considering the targeted alkylation of a phenolic hydroxy group and the pKa requirements of this

• reaction, weaker bases like potassium carbonate and cesium carbonate should theoretically suffice. However, the reaction outcomes with these two bases did not meet the desired expectations, as some starting material remained after 5 hours of reaction. Extending the reaction time did not lead to full

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

• Wei-Jin Chang,
• Sook Yee Liew,
• Thomas Kurz and
• Siow-Ping Tan

Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46

• hydantoins [19][20], we aim towards creating a more efficient procedure to access hydantoins. We are interested in the synthesis of hydantoins from amino acids and potassium cyanate in water due to its simplicity and environmental friendliness, which also precludes the use of water-sensitive and highly toxic

• potassium cyanate (25 mmol) and irradiated in an Anton–Paar Monowave 400 microwave reactor at 80 °C for 1 hour. Upon completion of the N-carbamylation reaction, as confirmed by TLC analysis, the reaction mixture was treated with concentrated hydrochloric acid (7 mL) and microwave irradiated at 80 °C for 15

• -phenylalanine with the corresponding amino acid to obtain H2b,c and H2e,f. General procedure for the synthesis of (S)-5-((2,5-dioxoimidazolidin-4-yl)methyl)-1H-imidazol-3-ium chloride (H2d) A 30 mL microwave reactor vial was charged with ʟ-histidine (5 mmol), distilled water (7 mL), and potassium cyanate (25

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• equivalent of 7a and 5.0 equivalents of 16a in the presence of stoichiometric potassium carbonate and 1.0 mol % of 9. When bromonium salt 9a was applied to the reaction, the desired product was obtained in 83% yield with 77% ee but almost no diastereoselectivity. The iodonium salt 9b also worked well and the

• chiral halonium salt. Next, the reaction temperature was optimized, and −40 °C was found to be optimal (Table 1, entries 7–9). Further optimization of the reaction conditions (amounts of potassium carbonate and pre-nucleophile, catalyst loading, and concentration) were conducted, and the reaction with

• 5.0 equivalents of pre-nucleophile and 1.0 equivalent of potassium carbonate in the presence of 1.0 mol % of 9 at 0.025 M of toluene and −40 °C was found to be optimal (Table 1, entries 10–13). Five equivalents of pre-nucleophile are required to obtain higher yields and enantioselectivities. Next, the

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• neurotransmitters [10][11] or as switching units for potential dependent potassium channels [12]. Compared to the Z → E conversion rate of 92% (in n-hexane) of the parent diazocine the conversion in water/DMSO mixtures is decreasing with increasing water concentration (73% in water/DMSO 9:1) [8][9][10][11][12

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

• Kirill A. Gomonov,
• Vasilii V. Pelipko,
• Igor A. Litvinov,
• Ilya A. Pilipenko,
• Anna M. Stepanova,
• Nikolai A. Lapatin,
• Ruslan I. Baichurin and
• Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

• ]. In addition, we have previously demonstrated the effective use of alkyl 3-bromo-3-nitroacrylates in the preparation of condensed furancarboxylates using potassium acetate as a catalyst [28][29][30]. The present study is aimed at developing methods for the synthesis of a wide range of condensed

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation

• Takeshi Fujita,
• Haruna Yabuki,
• Ryutaro Morioka,
• Kohei Fuchibe and
• Junji Ichikawa

Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8

• at the 4-position (2d) also produced high yields (94–98%). For arylboronic acid 2f, which has a methoxy group at the 4-position, the use of potassium phosphate as a base resulted in a 94% yield of 3bf. For arylboronic acid 2g, which features a strongly electron-withdrawing trifluoromethyl group, we

• optimized the coupling reaction using potassium phosphate as a base and increasing the nickel catalyst loading to 20 mol %, achieving a yield of 78% for the desired product 3bg. When 2-naphthylboronic acid (2i) was employed, its solubility was enhanced using a mixed solvent system of toluene, methanol, and

Cu(OTf)₂-catalyzed multicomponent reactions

• Sara Colombo,
• Camilla Loro,
• Egle M. Beccalli,
• Gianluigi Broggini and
• Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

• alkyltrifluoroborate into its corresponding alkyl radical. o-Halo-substituted aryl selenides and sulfides 13 can be achieved by a three-component coupling reaction performed with an aryne precursor, potassium halides and electrophilic chalcogen species as reactants, in the presence of Cu(OTf)2 (Scheme 10) [23]. Under

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• reaction (Table 1, entry 1) [4]. In the presence of potassium carbonate, only starting material 4a was detected. A stronger base to generate the nucleophilic intermediate was tested, and sulfonamide 5aa was detected in trace amounts (Table 1, entry 2). Considering the low solubility of the hypervalent

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

• Yuki Nakanishi,
• Shoichi Sugita,
• Kentaro Okano and
• Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

• conditions. We carried out the palladium-catalyzed intramolecular coupling reaction of precursor 1a under similar conditions [23], which afforded smooth reaction with phenanthroline bisamide, with 10 mol % of palladium acetate as a catalyst in the presence of potassium carbonate and tetra-n-butylammonium

• resulted in a decreased yield (27%) (Table 1, entries 4 and 5). It was found that increasing the amount of potassium carbonate to a three-fold excess improved the yield of 2a to 59% in the reaction at 110 °C shown in entry 6 of Table 1. Next, the effect of the ligand of the palladium catalyst was examined

• . Experimental Typical experimental procedure for the C–H arylation of pyridine derivative 5-octyldibenzo[b,f][1,7]naphthyridin-6(5H)-one (2a): To a screw-capped test tube equipped with a magnetic stirring bar were added amide 1a (44.1 mg, 0.100 mmol), potassium carbonate (42.0 mg, 0.304 mmol

Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling

• John M. Halford-McGuff,
• Thomas M. Richardson,
• Aidan P. McKay,
• Frederik Peschke,
• Glenn A. Burley and
• Allan J. B. Watson

Beilstein J. Org. Chem. 2024, 20, 3198–3204, doi:10.3762/bjoc.20.265

• functional groups for subsequent product diversification (Scheme 1). For example, protected alkynylboron reagents can be employed [35][36][37], such as N-methyliminodiacetic acid (MIDA)boronate esters [38], potassium trifluoroborates [39], and others [40][41][42]. Similarly, organosilicon reagents have

Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

• Thierry Milcent,
• Pascal Retailleau,
• Benoit Crousse and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

• can be noticed that the presence of an amino acid is compatible with the conditions of the reaction and did not interfere or significantly decrease the yield of the reaction (Scheme 3). Then, the N-carboxylate hydrazides 5a–d were firstly oxidized with iodine in the presence of potassium carbonate to

• on an intramolecular Michael addition carried out in DMF and catalyzed by 10% of potassium carbonate. As previously observed [37], under these conditions, the 5-endo-trig cyclization was selective and the lactam resulting from the 5-exo-trig cyclization was not observed. Furthermore, in the case of

Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins

• Mike Brockmann,
• Jonas Lobbel,
• Lara Unterriker and
• Rainer Herges

Beilstein J. Org. Chem. 2024, 20, 2954–2958, doi:10.3762/bjoc.20.248

• 4 (65%), 5 (50%), and 6 (40%) by chromatography was straightforward. However, the subsequent oxidation of the alcohol with the usual oxidizing agents (Jones reagent, KMnO4, etc.) was not successful. A radical oxidation with TEMPO, potassium bromide (KBr), sodium hypochlorite (NaOCl), and sodium

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• solution (10 mg mL−1 in CHCl3) of the semiconductor material was deposited by spin-coating at 1000 rpm for 60 seconds. Synthesis Compound 2a 16,17-Dihydroxyviolanthrone (500 mg, 1.02 mmol) and 2-ethylhexyl bromide (550 μL, 3.06 mmol) were dissolved in N,N-dimethylformamide (30 mL). Then, potassium

• mmol) and 1-bromooctane (2.12 mL, 12.28 mmol) were dissolved in N,N-dimethylformamide (60 mL). Then, potassium carbonate was added (1.13 g, 8.19 mmol), and the reaction mixture was stirred at 100 °C overnight. After cooling the reaction mixture to room temperature, it was poured into methanol (400 mL

• ]+ calcd for C50H48NaO4, 753.3409; found, 735.3445. Compound 2c 16,17-Dihydroxyviolanthrone (500 mg, 1.02 mmol) and 1-bromododecane (800 μL, 3.06 mmol) were dissolved in N,N-dimethylformamide (30 mL). Then, potassium carbonate was added (300 mg, 2.04 mmol), and the reaction mixture was stirred at 100 °C

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• solvent, whereas the arylation of ammonia was achieved by using ethyl acetate as solvent along with potassium carbonate as a base. Likewise, water was arylated using cesium carbonate as a base. The N-arylation reactions were performed under strict anhydrous conditions. The reported mechanistic hypothesis

• of O3-arylated galactosides 64 by reacting benzyl-protected galactoside 63 with diphenyliodonium triflates 16 at room temperature in the presence of potassium tert-butoxide as the base (Scheme 26) [77]. This transition-metal-free approach simplifies the synthesis process. Electron-pushing and

• 101 for the S-arylation of potassium O-alkyl xanthates 100 offers a simpler approach [95]. This method operates under mild conditions, facilitating the creation of substituted S-aryl xanthates 102 (Scheme 41). Utilizing diaryliodonium salts for the arylation of xanthate anions provides a pathway for

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

• steps from indigo (1a). The reaction of 1a with potassium permanganate afforded product 12 which was transformed to dehydroindigo (13) by pyridine-mediated elimination of acetic acid. The reaction of 13 with tetra-O-trimethylsilyl-ʟ-rhamnopyranose (4b) in the presence of trimethylsilyl iodide, addition

Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates

• Kento Iwai,
• Akari Hikasa,
• Kotaro Yoshioka,
• Shinki Tani,
• Kazuto Umezu and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2024, 20, 2827–2833, doi:10.3762/bjoc.20.238

• (Table 3, entry 2). Indeed, using THF that had not been dried as purchased resulted in a significant increase of the yield to 82% (Table 3, entry 3). The choice of base was also crucial (Table 3, entries 3–5). While the yield of 5a was low with potassium tert-butoxide, a yield of 66% using lithium tert

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

• Jonas Holste,
• Paul Weldon,
• Donald Boyer and
• Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

• shaken for 15 min and then placed in an oven at 100 °C until the silica gel was completely dried. The impregnated silica gel was stored in the dark until use. Syntheses 1-(1-Propen-1-yl)piperidine (2): In a manner analogous to [27], potassium carbonate (2 g, 15 mmol), piperidine (10 mL, 0.1 mol), and

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

• -acylimidazoles with potassium alkenyl trifluoroborates under mild electrochemical conditions (Scheme 41). This method provides an efficient and enantioselective approach to C(sp3)–H alkenylation, demonstrating the potential of combining chiral catalysis with electrochemistry for the functionalization of complex

Cell-free protein synthesis with technical additives – expanding the parameter space of in vitro gene expression

• Tabea Bartsch,
• Stephan Lütz and
• Katrin Rosenthal

Beilstein J. Org. Chem. 2024, 20, 2242–2253, doi:10.3762/bjoc.20.192

• the magnesium and potassium glutamate concentration, is 140 mM, which is less than half the concentration reported for the cellular environment. The cytoplasmic osmolarity of about 600 mOsm [16] is 50% higher than that calculated for CFPS. Taking into account all defined components, the water content

• for the calculation of the macromolecular concentration of the CFPS mix. Magnesium and potassium glutamate were considered as the contributing inorganic ions for the reference composition, for the DES corresponding salts were added to the value of 140 mM. For the osmolarity the concentrations of all

• defined components were multiplied with their number of dissociated particles, which was assumed as 1 for most components and 2 for magnesium and potassium glutamate and combined with the calculated concentration of macromolecules. For the water content, the amount of all known components was subtracted

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• generated by altering the reaction conditions during synthesis [52][53][54][55][56][57] or by using potassium chloride or ammonium fluoride salts as additives [58][59][60]. In a comprehensive study [61], the catalytic properties of three types (rope, rod and fibre) of mesoporous silica Santa Barbara

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• give 1,5-diacyl-5-hydroxypyrazolines 131. Cleavage of the protecting group with potassium carbonate in methanol finally provides the corresponding 5-acyl NH-pyrazoles 132 (Scheme 46) [149]. A novel approach to synthesizing pyrazoles via the initial formation of isoxazoles 138 through (3 + 2

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

• ) [43]. In parallel, Sheng and Zhang et al. found that 2-(1,3,4-oxadiazol-2-yl)aniline derivatives 38 could be electrochemically synthesized from isatins 35 and acylhydrazine 36. The transformation was carried out in an undivided cell at high temperature in DMSO using potassium iodide as supporting

• electrolyte with potassium carbonate as a base and two platinum electrodes. Mechanistically, condensation of the two reactants formed isatin-derived acylhydrazone 37. Hydrolysis of the latter in the presence of the inorganic base gave rise to potassium carboxylate 39. Meanwhile, two consecutive SET oxidations

• -triazoles was accomplished by D. Tang et al. through the formal cycloaddition between in situ-generated aldehyde-derived hydrazones and cyanoamine (70). The 5-amino derivatives 71 were obtained in moderate to good yields by employing potassium iodide as electrocatalyst (Scheme 13) [55]. Herein, the

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• -substituted indazole analogs in 44% and 40% yields, respectively, by treating compound 6 with methyl iodide and potassium carbonate in dimethylformamide (DMF) at room temperature for 17 h [40]. Other works have shown poor selectivity when 6 and other isomers similar to 6 were reacted with isopropyl iodide and

• potassium carbonate, isopropyl bromide and cesium carbonate, and bromocyclohexane with potassium carbonate, and only afforded yields not higher than 52% in various solvents [41][42][43]. Recently, Alam and Keeting [37] explored the regioselectivity in the alkylation of variously substituted indazoles