Synthesis of diaryl phosphates using phytic acid as a phosphorus source

• Kazuya Asao,
• Seika Matsumoto,
• Haruka Mori,
• Riku Yoshimura,
• Takeshi Sasaki,
• Naoya Hirata,
• Yasuyuki Hayakawa and
• Shin-ichi Kawaguchi

Beilstein J. Org. Chem. 2026, 22, 213–223, doi:10.3762/bjoc.22.15

• A total P analysis was performed according to a test method for industrial wastewater standardized in the Japanese Industrial Standards (JIS K 0102 46.3). Step 1 (preparation of a coloring agent): Hexaammonium heptamolybdate tetrahydrate (300 mg) and antimony potassium tartrate trihydrate (12 mg

• potassium peroxodisulfate aqueous solution (4.0 w/v %, 5 mL) was added to the diluted phytic acid solution (25 mL), and the resulting mixture was autoclaved (121 °C, 30 min). Thereafter, the solution was diluted with deionized water to a concentration of approximately 1 µg P/mL. Step 3 (measurements): The

• standard curve was constructed using potassium dihydrogen phosphate solutions (0.5, 1.0, and 1.5 µg P/mL) as the standard solutions. Diaryl phosphate synthesis and characterization The synthesis methods for diaryl phosphates using commercial and extracted phytic acid are included in Supporting Information

Improved synthesis and physicochemical characterization of the selective serotonin 2A receptor agonist 25CN-NBOH

• Adrian G. Rossebø,
• Hannah G. Kolberg,
• Anders E. Tønder,
• Louise Kjaerulff,
• Poul Erik Hansen,
• Karla A. Frydenvang,
• Jesper Østergaard and
• Jesper L. Kristensen

Beilstein J. Org. Chem. 2026, 22, 175–184, doi:10.3762/bjoc.22.11

• scenarios. Experimental Reagents and solvents were used as received from commercial vendors, unless otherwise specified. ortho-Phosphoric acid (85%, Ph. Eur.), potassium chloride, sodium carbonate (>99.9%), and sodium dihydrogen phosphate monohydrate (Ph. Eur.) were purchased from Merck (Darmstadt, Germany

• = 0.15 M), 67 mM sodium phosphate (pH 7.40, I = 0.18 M), and 50 mM sodium carbonate (pH 9.50, I = 0.15 M). The ionic strength of the buffers was adjusted by adding a calculated amount of potassium chloride. The octanol phases were saturated with the appropriate buffer solution, and vice versa, before the

Highly electrophilic, gem- and spiro-activated trichloromethylnitrocyclopropanes: synthesis and structure

• Ilia A. Pilipenko,
• Mikhail V. Grigoriev,
• Olga Yu. Ozerova,
• Igor A. Litvinov,
• Darya V. Spiridonova,
• Aleksander V. Vasilyev and
• Sergey V. Makarenko

Beilstein J. Org. Chem. 2026, 22, 123–130, doi:10.3762/bjoc.22.5

• conditions. The reaction is carried out either in tetrahydrofuran in the presence of triethylamine or in methanol in the presence of fused potassium acetate. The structures of the isolated individual products were characterized by 1H and 13C NMR, IR spectroscopy, mass spectrometry, and confirmed by single

Reactivity umpolung of the cycloheptatriene core in hexa(methoxycarbonyl)cycloheptatriene

• Dmitry N. Platonov,
• Alexander Yu. Belyy,
• Rinat F. Salikov,
• Kirill S. Erokhin and
• Yury V. Tomilov

Beilstein J. Org. Chem. 2026, 22, 64–70, doi:10.3762/bjoc.22.2

• potassium 1 (Figure 2) undergoes reactions with various electrophilic reagents which presented the first examples of unexpected pathways for the derivatization of cycloheptatrienes [17][18][19]. However, the anion is highly symmetric and does not challenge regioselectivity. Therefore, besides the

• revealed that the α-position is most nucleophilic. Notably, anion 1 demonstrated similar HOMO and Fukui function distribution (see Supporting Information File 1), however, all positions would lead to the very same products. The potassium salt of anion 2 was generated in an acetonitrile solution from hexa

• (methoxycarbonyl)cycloheptatriene 3 (pKa(DMSO) = 8.65) [20][21] with potassium tert-butoxide and subjected to reactions with electrophilic reagents. The reactions gave two primary products 4 and 5 (Scheme 1) through an attack to either the most available i-position or the most nucleophilic but sterically hindered

Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review

• Daniel S. Müller

Beilstein J. Org. Chem. 2026, 22, 1–63, doi:10.3762/bjoc.22.1

• reported the synthesis of conjugated alkenyl chloride 183 by chlorination of cis-diol 181 and subsequent elimination of product 182 with KOH (Scheme 31) [130]. Schlosser reported that treatment of 1,2-dichloroalkanes with sodium or potassium hydroxide in dimethoxyethane effected selective elimination

• oxidation of HCl with oxone (potassium peroxymonosulfate) to generate molecular chlorine (Scheme 35A) [135]. Electrophilic addition of chlorine across the enone double bond, followed by triethylamine-induced elimination, furnished the corresponding alkenyl chlorides (e.g., compound 193) in good yields. A

Sustainable electrochemical synthesis of aliphatic nitro-NNO-azoxy compounds employing ammonium dinitramide and their in vitro evaluation as potential nitric oxide donors and fungicides

• Alexander S. Budnikov,
• Nikita E. Leonov,
• Michael S. Klenov,
• Andrey A. Kulikov,
• Igor B. Krylov,
• Timofey A. Kudryashev,
• Aleksandr M. Churakov,
• Alexander O. Terent’ev and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2025, 21, 2739–2754, doi:10.3762/bjoc.21.211

• , entry 4). Increasing the current density resulted in a drop in the yield to 32%, while reducing the current density had a negligible effect on the yield of 2a (Table 1, entry 5). Employing 1 equivalent of ADN or potassium dinitramide (KDN) along with 1 equivalent of n-Bu4NBF4 as the supporting

Recent advancements in the synthesis of Veratrum alkaloids

• Morwenna Mögel,
• David Berger and
• Philipp Heretsch

Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206

• regioselectively desaturated to furnish known phenylsulfonylenamine (Scheme 23). Conversion toward the bromohydrin, treatment with potassium hydride, and subsequent addition of the crotyl-Grignard reagent 75 gave the desired isomer 76 in 22% yield over four steps. More exactly, the diastereomeric piperidine was

Synthesis of new tetra- and pentacyclic, methylenedioxy- and ethylenedioxy-substituted derivatives of the dibenzo[c,f][1,2]thiazepine ring system

• Gábor Berecz,
• András Dancsó,
• Mária Tóthné Lauritz,
• Loránd Kiss,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2645–2656, doi:10.3762/bjoc.21.205

• of compound 28 with 1,2-dibromoethane (29), reduction with NaBH4 (30), chlorination with SOCl2 (31) and subsequent treatment with methylamine afforded pentacyclic product 25. Reaction of bromoalkyl derivative 30 with potassium thioacetate gave acetylthio derivative 32, which was cyclized after

Chemoenzymatic synthesis of the cardenolide rhodexin A and its aglycone sarmentogenin

• Fuzhen Song,
• Mengmeng Zheng,
• Dongkai Wang,
• Xudong Qu and
• Qianghui Zhou

Beilstein J. Org. Chem. 2025, 21, 2637–2644, doi:10.3762/bjoc.21.204

• lactone ring attached to the C17 position, and a glycosyl moiety in general. It is believed that CGs can increase cardiac contractility by inhibiting the sodium–potassium adenosine triphosphatase (Na+/K+ ATPase) of the plasma membrane [2]. The well-known CGs, such as digoxin, digitoxin, ouabain, and

Silica gel with covalently attached bambusuril macrocycle for dicyanoaurate sorption from water

• Michaela Šusterová and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2025, 21, 2604–2611, doi:10.3762/bjoc.21.201

• 1.15111) was dried in vacuo at 50 °C overnight before use. 3-Aminopropyltriethoxysilane (APTES), 1-hydroxybenzotriazole (HOBt), 1,3-diisopropylcarbodiimide (DIC), potassium dicyanoaurate, potassium dicyanoargentate, sodium chloride, tetrabutylammonium chloride and sodium bromide were purchased from Merck

Visible-light-driven NHC and organophotoredox dual catalysis for the synthesis of carbonyl compounds

• Vasudevan Dhayalan

Beilstein J. Org. Chem. 2025, 21, 2584–2603, doi:10.3762/bjoc.21.200

• , and aryloxymethyl potassium trifluoroborate salt 10 under mild conditions. The described catalytic system exhibited broad functional group tolerance and efficiently employed terminal alkenes 11 to generate quaternary centers adjacent to the carbonyl group. The key step in this organocatalytic process

Effect of a photoswitchable rotaxane on membrane permeabilization across lipid compositions

• Udyogi N. K. Conthagamage,
• Lilia Lopez,
• Zuliah A. Abdulsalam and
• Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2498–2512, doi:10.3762/bjoc.21.192

• bilayers through the shuttling of the macrocycle carrying the ions or through a relay mechanism [10][11]. In one example, the isomerization of an azobenzene photoswitch incorporated into the axle was used to modulate the shuttling rate of the macrocycle and, consequently, the efficiency of potassium ion

Assembly strategy for thieno[3,2-b]thiophenes via a disulfide intermediate derived from 3-nitrothiophene-2,5-dicarboxylate

• Roman A. Irgashev

Beilstein J. Org. Chem. 2025, 21, 2489–2497, doi:10.3762/bjoc.21.191

• to be an unsuitable route for nucleophilic substitution of its nitro group. Next, we explored an alternative route using potassium thioacetate (KSAc) as a softer nucleophile. Unexpectedly, the reaction of ester 1 with KSAc in acetone gave a mixture of products other than the desired 3-AcS-substituted

• addition to potassium thioacetate, the reactivity of ester 1 was investigated with other related S-nucleophiles, such as potassium ethyl xanthate (KSC(S)OEt), sodium diethyldithiocarbamate (NaSC(S)NEt2) as well as thioacetamide in the presence of K2CO3 and Na2S2 (Table 1, entries 2–5). In each case, the

• . Conclusion In summary, this study reveals an unusual and previously poorly understood reactivity of 3-nitrothiophene-2,5-dicarboxylate toward sulfur-containing nucleophiles such as potassium thioacetate or thioacetamide, which resulted in the efficient formation of both bis(thiophen-3-yl) sulfide and

Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds

• Natalya Akhmetdinova,
• Ilgiz Biktagirov and
• Liliya Kh. Faizullina

Beilstein J. Org. Chem. 2025, 21, 2416–2446, doi:10.3762/bjoc.21.185

• Me2S to give dialdehyde 28 and reaction of compound 28 with colloidal potassium in toluene. During aldol condensation in the presence of morpholine-camphorsulfonic acid (CSA) or ʟ-proline, a stable aldehyde 30 was isolated in yields of 50% and 75%, respectively. Decarbonylation and corresponding

Thiadiazino-indole, thiadiazino-carbazole and benzothiadiazino-carbazole dioxides: synthesis, physicochemical and early ADME characterization of representatives of new tri-, tetra- and pentacyclic ring systems and their intermediates

• Gyöngyvér Pusztai,
• László Poszávácz,
• Anna Vincze,
• András Marton,
• Ahmed Qasim Abdulhussein,
• Judit Halász,
• András Dancsó,
• Gyula Simig,
• György Tibor Balogh and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2220–2233, doi:10.3762/bjoc.21.169

• microsome (HLM) fractions were thawed on ice and diluted in 0.05 M potassium phosphate buffer (pH 7.4) to a final protein concentration of 1.25 mg/mL. Test compounds were dissolved in DMSO to create stock solutions of 5 mM. The drug concentration in the final assays was 10 μM. The assay was performed in

Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs

• Almaz A. Zagidullin,
• Emil R. Bulatov,
• Mikhail N. Khrizanforov,
• Damir R. Davletshin,
• Elvina M. Gilyazova,
• Ivan A. Strelkov and
• Vasily A. Miluykov

Beilstein J. Org. Chem. 2025, 21, 1909–1916, doi:10.3762/bjoc.21.148

• equiv of potassium hydroxide (34.0 g, 0.607 mol) were added to the flask. Methylphosphonic dichloride MeP(O)Cl2 (1 equiv, 19.2 g, 0.144 mol) was added dropwise to the mixture with constant stirring in 1 hour. The reaction mixture was additionally stirred at −25 to −30 °C for 2 h and precipitating for 12

• mol) and 4.2 equiv of potassium hydroxide (31.8 g, 0.567 mol) were added to the flask. Methyl dichlorophosphate (MeO)P(O)Cl2 (1 equiv, 20.1 g, 0.135 mol) was added dropwise to the mixture with constant stirring in 1 hour. The reaction mixture was additionally stirred at −25 to −30 °C for 2 h and

• with 200 mL of dichloromethane, equipped with a mechanical stirrer, was cooled to −30 °C. Then, 3 equiv of glycidol (22.6 g, 0.305 mol) and 4.5 equiv of potassium hydroxide (25.6 g, 0.457 mol) were added to the flask. Phosphorus oxychloride P(O)Cl3 (1 equiv, 15.6 g, 0.102 mol) was added dropwise to the

Influence of the cation in hypophosphite-mediated catalyst-free reductive amination

• Natalia Lebedeva,
• Fedor Kliuev,
• Olesya Zvereva,
• Klim Biriukov,
• Evgeniya Podyacheva,
• Maria Godovikova,
• Oleg I. Afanasyev and
• Denis Chusov

Beilstein J. Org. Chem. 2025, 21, 1661–1670, doi:10.3762/bjoc.21.130

• system is more efficient than the earlier described usage of the pure NaH2PO2: higher solubility of the potassium, rubidium and cesium salts compared to the sodium and lithium and a proper pH of the reaction medium. Acidic catalysis strongly accelerates the rate of hemiaminal and iminium ion formation

• [41]. The higher ionic radius of potassium facilitates rapid dissolution of the reducing agent thus increasing the reduction rate. Together these factors allow conducting reductive amination reactions selectively and at lower temperatures. Conclusion In conclusion, the reactivity of hypophosphites of

Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds

• Lidia Zaharieva,
• Vera Deneva,
• Fadhil S. Kamounah,
• Nikolay Vassilev,
• Ivan Angelov,
• Michael Pittelkow and
• Liudmil Antonov

Beilstein J. Org. Chem. 2025, 21, 1404–1421, doi:10.3762/bjoc.21.105

• adding pre-cooled methanol (4.0 mL). In a separate round-bottomed flask, 7-hydroxyquinoline (0.29 g, 2.0 mmol) and potassium hydroxide (0.163 g, 3.0 mmol) were dissolved in methanol (6.0 mL) and cooled to 0 °C. This solution was treated under constant stirring by dropwise addition of the cold diazonium

• a separate 50 mL flask, 7-hydroxyquinoline (0.29 g, 2.0 mmol) dissolved in methanol (4.0 mL) was treated with potassium hydroxide (0.16 g, 3.0 mmol). The solution was stirred at 0 °C for 20 min, then the cooled diazonium salt solution was added slowly to the cold solution of 7-hydroxyquinoline

• during 30 min. Upon addition, a red-orange color formed. The mixture was left stirring at 0 °C for 2 h, then at rt overnight. The mixture was filtered, the filtrate was neutralized with 1 N aqueous potassium hydroxide solution, diluted with dichloromethane (75 mL) and stirred overnight. The orange solid

Oxetanes: formation, reactivity and total syntheses of natural products

• Peter Gabko,
• Martin Kalník and
• Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

• Jiangfei Chen,
• Yi-Lin Qu,
• Ming Yuan,
• Xiang-Mei Wu,
• Heng-Pei Jiang,
• Ying Fu and
• Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

Synthetic approach to borrelidin fragments: focus on key intermediates

• Yudhi Dwi Kurniawan,
• Zetryana Puteri Tachrim,
• Teni Ernawati,
• Faris Hermawan,
• Ima Nurasiyah and
• Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

• acetate functionality using potassium carbonate in methanol, followed by reaction with tosyl chloride in pyridine and DMAP. The product, ent-43, was obtained in 79.5% yield over three steps. This compound was reduced using LiAlH4 and treated with TBAF to remove the TBDMS group, yielding alcohol ent-40 in

• in 96% yield. Hydrolysis of the acetate group in 69 with potassium carbonate followed by treatment with TBDMSCl and imidazole converted it into silyl ether 70. The ester group in 70 was then hydrolyzed using lithium hydroxide, and the resulting acid was coupled with Evans’ chiral oxazolidinone in the

Gold extraction at the molecular level using α- and β-cyclodextrins

• Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

• even non-ore sources (e.g., mining wastes) [18] and abandoned electrical and electronic equipment, called e-waste, which can contain up to ten times more gold than waste ores [19]. To retrieve gold from these materials, the most widespread process is to use potassium or sodium cyanides, which are the

• precious metals [42]. The process of gold precipitation with cyclodextrins, bromic acid and potassium hydroxide to form the potassium bromoaurate salt was patented, with patent coverage expanding to metals like silver, platinum, palladium, and rare earths, as well as the use of other cyclodextrins, β- and

• γ-CDs, other acids (including hydrogen halides, nitric acid, sulfuric acid, and mixtures thereof) and sodium hydroxide (instead of potassium hydroxide) [43]. Scale-up pilot trials on 20 batch samples were conducted in Arizona with partnership from companies already active in the market. Results

Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C–N bond axial chirality

• Natsume Akimoto,
• Kaho Takaya,
• Yoshio Kasashima,
• Kohei Watanabe,
• Yasushi Yoshida and
• Takashi Mino

Beilstein J. Org. Chem. 2025, 21, 1018–1023, doi:10.3762/bjoc.21.83

• (Table 1, entry 5). Other potassium salts such as K3PO4 led to a low yield of the product (Table 1, entry 6). Meanwhile, when Na3PO4 was tested, the yield decreased, but the enantioselectivity improved to 88% ee (Table 1, entry 7). With Na3PO4 as the optimum base, which showed the highest

Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline

• Benedek Batizi,
• Patrik Pollák,
• András Dancsó,
• Péter Keglevich,
• Gyula Simig,
• Balázs Volk and
• Mátyás Milen

Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79

• ammonium derivative 14 with the potassium salt of compound 15 resulted in the ring-opened derivative 16. Removal of the benzylthiocarbonyl moiety, then Beckmann rearrangement of the oxime obtained from ketone 17 and subsequent cyclization gave β-carboline derivative 18, which was dehydrogenated and

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