Asymmetric Mannich reaction of aromatic imines with malonates in the presence of multifunctional catalysts

• Kadri Kriis,
• Harry Martõnov,
• Annette Miller,
• Mia Peterson,
• Ivar Järving and
• Tõnis Kanger

Beilstein J. Org. Chem. 2026, 22, 151–157, doi:10.3762/bjoc.22.8

• stirred at room temperature until a suspension was formed (ca 5 min). After that, the reaction mixture was cooled to −20 °C. The malonic ester (0.171 mmol, 3.0 equiv) was added to the reaction vessel via syringe. The reaction was stirred at −20 °C for an appropriate time. The progress of the reaction was

Design and synthesis of an axially chiral platinum(II) complex and its CPL properties in PMMA matrix

• Daiki Tauchi,
• Sota Ogura,
• Misa Sakura,
• Kazunori Tsubaki and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2026, 22, 143–150, doi:10.3762/bjoc.22.7

• solutions (1.0 × 10−5 M) and 1 wt % PMMA matrices were acquired using a JASCO FP-8550 spectrometer at room temperature, at excitation wavelength of 300 nm (both solution and PMMA matrix). CPL spectra of CH2Cl2 solutions (1.0 × 10−5 M) and 1 wt % PMMA matrices were measured with a JASCO CPL-300

• spectrofluoropolarimeter at room temperature, at a scattering angle of 0° upon excitation with unpolarized, monochromated incident light. Absolute PLQYs of solutions and powder samples were determined using a JASCO FP-8550 spectrometer with an integrating sphere (JASCO ILF-533, diameter 96 mm) at an excitation wavelength

• (112 mg, 0.0962 mmol) and trimethylsilylacetylene (0.40 mL, 2.9 mmol) was added degassed solution of Et3N (2.6 mL, 19 mmol) and toluene (5.2 mL) by argon bubbling. The reaction mixture was refluxed at 90 °C for 21 hours. After cooling to room temperature, the reaction mixture was filtered through

Total synthesis of natural products based on hydrogenation of aromatic rings

• Haoxiang Wu and
• Xiangbing Qi

Beilstein J. Org. Chem. 2026, 22, 88–122, doi:10.3762/bjoc.22.4

• aromatic rings (Scheme 4) [48]. Using [Rh(nbd)Cl]2 and Pd/C as catalysts, aromatic hydrocarbons with various functional groups can be hydrogenated at room temperature and 1 atmosphere of hydrogen, thus simplifying the reaction operation and cost. Hydrogenation of fused aromatic rings Hydrogenation of the

Advances in Zr-mediated radical transformations and applications to total synthesis

• Hiroshige Ogawa and
• Hugh Nakamura

Beilstein J. Org. Chem. 2026, 22, 71–87, doi:10.3762/bjoc.22.3

• tryptophan. The resulting radical species underwent fast dimerization to furnish the desired dimer 61. This zirconocene-catalyzed dimerization proceeded smoothly under remarkably mild conditions at room temperature, suggesting broad applicability. Indeed, the reaction was shown to tolerate a wide substrate

• potential and stabilizing the radical pathway. The DFT calculations are shown in Scheme 13A. The activation barrier for the XAT process was calculated to be ΔG‡ = 8.0 kcal/mol, indicating that this process can proceed spontaneously around room temperature. Moreover, the transition state (TS1) suggested the

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

• transition states with an adjacent ester group, not to the stability of the main conformer. Conversely, the reactions with halogens and diazonium salts are immediate at room temperature and the α-selectivity, when observed, can be due to the stability of the main conformer. The transition from iodine to

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

• of the desired products (Scheme 20B). The authors proposed that BTC functions by regenerating benzoyl chloride in situ from benzoic acid, thereby allowing the use of benzoyl chloride in catalytic quantities (Scheme 20C). Under similar conditions – benzoyl chloride (2.2 equiv), room temperature

Competitive cyclization of ethyl trifluoroacetoacetate and methyl ketones with 1,3-diamino-2-propanol into hydrogenated oxazolo- and pyrimido-condensed pyridones

• Svetlana O. Kushch,
• Marina V. Goryaeva,
• Yanina V. Burgart,
• Marina A. Ezhikova,
• Mikhail I. Kodess,
• Pavel A. Slepukhin,
• Alexandrina S. Volobueva,
• Vladimir V. Zarubaev and
• Victor I. Saloutin

Beilstein J. Org. Chem. 2025, 21, 2716–2729, doi:10.3762/bjoc.21.209

• %) (Table 1, entry 10), with the formation of the cis,cis-bicycle 4acc as the predominant product (28%), while the proportion of hexahydrooxazolopyridones 5 was minimal (10%) compared to all other conditions. The highest content of hexahydrooxazolo[3,2-a]pyridin-5-one 5a was observed at room temperature in

Tandem hydrothiocyanation/cyclization of CF₃-iminopropargyl alcohols with NaSCN in the presence of AcOH

• Ruslan S. Shulgin,
• Ol’ga G. Volostnykh,
• Anton V. Stepanov,
• Igor’ A. Ushakov,
• Alexander V. Vashchenko and
• Olesya A. Shemyakina

Beilstein J. Org. Chem. 2025, 21, 2694–2702, doi:10.3762/bjoc.21.207

• MSCN/acid system. In comparison to ynamides [19] and alkynehydrazones [22], whose adducts cyclize with the involvement of nitrogen functional groups at elevated temperatures and extended reaction times, the reaction of CF3-substituted iminopropargyl alcohols occurred at room temperature within 15 min

• acetic acid. The reaction was carried out at room temperature and with vigorous stirring for 15 minutes. Next, the solvent was removed and the residue was purified using column chromatography (eluting with diethyl ether/hexane 1:8, then acetone/hexane 2:1 to give products 2 and 3. Procedure for oxidation

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

• resulted in a hydroxy group, which was oxidized to furnish Nazarov precursor 54 in 52% yield. Key step of this sequence was the photoinduced excited-state Nazarov reaction, which involved irradiation of 54 in dichloroethane at 366 nm for 30 min at room temperature. Remarkably, this method had been

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

• amorphous character of the compounds exhibiting wide melting ranges (21b, 38d, 54f) were proven by XRPD measurements performed on a PANalytical Empyrean X-ray powder diffractometer at room temperature. Powder samples (without grinding) were placed between two Mylar foils in the sample holder at a reflection

• to 0–5 °C, and SnCl4 (47.28 g, 182 mmol, 21.2 mL) was added to the reaction mixture. The red suspension obtained was stirred at 0–5 °C for 1 h, then at room temperature for 2 h. It was poured onto a mixture of crushed ice (1500 g) and conc. hydrochloric acid (200 mL). It was stirred while warming to

• room temperature (ca 3 h). The crystalline product separated was filtered, washed with diluted hydrochloric acid (5%, 2 × 50 mL) and water (2 × 50 mL), then air-dried to give crude 7 (17.6 g of off-white solid). The two-phase filtrate was separated, the strongly acidic aqueous phase was washed with DCM

Thiazolidinones: novel insights from microwave synthesis, computational studies, and potentially bioactive hybrids

• Luan A. Martinho,
• Victor H. J. G. Praciano,
• Guilherme D. R. Matos,
• Claudia C. Gatto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2025, 21, 2618–2636, doi:10.3762/bjoc.21.203

• experimental spectrum. In blue, suppressed or absent carbon atoms bound to hydrogen atoms. a) Visual impressions of the solvatochromic study in various solvents (10−5 M) after excitation with a natural light. b) UV–vis absorption spectra of 3n in different solvents (10−5 M) at room temperature. c) Normalized

• emission spectra of 3n in different solvents (10−5 M) at room temperature. d) Lippert–Mataga plot showing Stokes shift as a function of solvent orientation polarizability (Δf) for compound 3n. Photophysical study in aqueous solution under different pH values for compound 3n (10−5 M) at room temperature. a

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

• enables the highly regioselective formation of meta-acylated ketone products 16 through a radical pathway. The NHC-catalyzed novel acylation was achieved using acyl fluorides 4 and electron-rich arenes 15 in the presence of NHC (20 mol %), photocatalyst (5 mol %), and Cs2CO3 in CH3CN at room temperature

Pentacyclic aromatic heterocycles from Pd-catalyzed annulation of 1,5-diaryl-1,2,3-triazoles

• Kaylen D. Lathrum,
• Emily M. Hanneken,
• Katelyn R. Grzelak and
• James T. Fletcher

Beilstein J. Org. Chem. 2025, 21, 2524–2534, doi:10.3762/bjoc.21.194

• pentacyclic ring system. A general downfield shifting of the entire set of signals by no less than 0.5 ppm supports the expansion of the overall aromatic π-system upon annulation. Aromatic signal symmetry for non-annulated compounds 12 and 42 show a lack of distinct rotational isomers at room temperature on

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

• formation of liquid-ordered (Lo) domains [16]. To further assess the effect of membrane rigidity on rotaxane behavior, we also studied LUVs composed solely of DPPC lipids, which form a highly ordered gel phase (Lβ) at room temperature due to their saturated acyl chains [17]. Rotaxane 1 was incorporated into

• ). Similarly, in LUVs composed of pure DPPC, which adopts a highly ordered gel phase (Lβ) at room temperature [17], minimal release was observed: 7% with rotaxane 1-E, 3% with rotaxane 1-Z, 6% with rotaxane 2, and 4% with axle 3 (Table 1, Figure 4a, and Supporting Information File 1, Figures S1d and S10). Our

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

• 3) was used as solvent, the reduction of disulfide 3 with NaBH4 proceeded more efficiently at reflux for 2 h. The reaction mixture was then treated with K2CO3 and the alkylating agent at room temperature. The product was identified as the desired 3-benzylthio-substituted thiophene-2,5-dicarboxylate

• reactions, probably involving ester hydrolysis or alkylating agent decomposition, can be avoided by omitting the external base. In addition, Na2S2O4 was investigated as a reductant in a DMF/water 9:1 (v/v) mixture at room temperature (Table 2, entry 6). In the presence of both K2CO3 and the alkylating agent

• also gave product 7a in about 25% yield, along with the formation of a mixture of byproducts. It was found that the most favorable conditions for cyclization of compounds 4a, 4b, and 5a were their treatment with excess LiH in a solution of dry DMF at room temperature for 24 h. In this way, products 7a

Palladium-catalyzed regioselective C1-selective nitration of carbazoles

• Vikash Kumar,
• Jyothis Dharaniyedath,
• Aiswarya T P,
• Sk Ariyan,
• Chitrothu Venkatesh and
• Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2025, 21, 2479–2488, doi:10.3762/bjoc.21.190

• NiCl2/NaBH4 in methanol at room temperature, affording the corresponding amine 4 in 93% yield. To align with green chemistry principles, we employed a recently reported mechanochemical protocol by Ito and co-workers for the reduction of nitro compounds to amines [72]. Using this solvent-free method

• , 1.2 equiv). Then, the solvent 1,4-dioxane (2.0 mL) was added, and the reaction mixture was allowed to stir in a preheated oil bath at 120 °C for 24 h. Upon completion of the reaction time, the reaction mixture was cooled to room temperature and diluted with dichloromethane (10 mL). The reaction

Ex-situ generation of gaseous nitriles in two-chamber glassware for facile haloacetimidate synthesis

• Nikolai B. Akselvoll,
• Jonas T. Larsen and
• Christian M. Pedersen

Beilstein J. Org. Chem. 2025, 21, 2465–2469, doi:10.3762/bjoc.21.188

• [14][15][16][17]. Recently, 2,2,2-trifluoroacetaldehyde O-(aryl)oxime has been introduced as a precursor for trifluoroacetonitrile allowing to work under mild conditions at room temperature (Figure 1) [18]. Whether one prepares a precursor or the actual reagent, a separate setup is needed and hence

• conclusion, we have developed a simple and safe methodology for the on-demand ex situ generation of stoichiometric amounts of gaseous haloacetonitriles in a closed system at room temperature. The methodology is safe, robust, and operationally simple on a laboratory scale. The method was exemplified by the

Catalytic enantioselective synthesis of selenium-containing atropisomers via C–Se bond formations

• Qi-Sen Gao,
• Zheng-Wei Wei and
• Zhi-Min Chen

Beilstein J. Org. Chem. 2025, 21, 2447–2455, doi:10.3762/bjoc.21.186

• reaction yielded the desired product at room temperature with high regioselectivity and stereoselectivity (E/Z ratio >99:1). Notably, when chiral catalyst (cat.1) was used, the reaction afforded the axially chiral product 9 in 43% yield with 84% ee. The proposed mechanism proceeds as follows. Catalyst cat

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

• have been little studied, and are of interest to synthetic chemists. Thus, the interaction of (−)-metaphanine (70) with ammonia in CH3OH at room temperature led to the in situ formation of imine 72, which, as a result of an intramolecular aza-benzilic acid-type rearrangement, was converted in more than

The high potential of methyl laurate as a recyclable competitor to conventional toxic solvents in [3 + 2] cycloaddition reactions

• Ayhan Yıldırım and
• Mustafa Göker

Beilstein J. Org. Chem. 2025, 21, 2389–2415, doi:10.3762/bjoc.21.184

• experiment was conducted in which a series of organic solvents and water were subjected to solubility tests. For the purposes of this experiment, approximately 15 mg of nitrone was mixed with 1 mL of solvent in a 10 mL test tube at room temperature (22 °C). As demonstrated in Figure 8c, the solvents under

• completely consumed. Subsequently, the reaction mixture was cooled to room temperature and hexane was added with rapid stirring, allowing the cycloaddition product to precipitate as a mixture of cis and trans diastereoisomers in the form of a white solid. The precipitate was then washed with a small quantity

An Fe(II)-catalyzed synthesis of spiro[indoline-3,2'-pyrrolidine] derivatives

• Elizaveta V. Gradova,
• Nikita A. Ozhegov,
• Roman O. Shcherbakov,
• Alexander G. Tkachenko,
• Larisa Y. Nesterova,
• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2025, 21, 2383–2388, doi:10.3762/bjoc.21.183

• model ketone oxime acetate from β-3-indolyl ketone 3a using the previously described telescopic protocol [17]. This substrate was subjected to FeCl2-catalyzed spirocyclization in acetonitrile at room temperature, affording the desired spirocyclic product 4a in 70% yield as a mixture of diastereomers (dr

Rotaxanes with integrated photoswitches: design principles, functional behavior, and emerging applications

• Jullyane Emi Matsushima,
• Khushbu,
• Zuliah Abdulsalam,
• Udyogi Navodya Kulathilaka Conthagamage and
• Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2345–2366, doi:10.3762/bjoc.21.179

• stiff-stilbene facilitated the formation of aggregates, resulting in organic room-temperature phosphorescence. The phosphorescent properties can be modulated by inducing macrocycle translation through acid–base stimuli or by disrupting the aggregates via stiff-stilbene photoisomerization. The authors

Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis

• Peng-Xi Luo,
• Jin-Xuan Yang,
• Shao-Min Fu and
• Bo Liu

Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177

• blue LEDs at room temperature constructed a single diastereoisomer 23 in 90% yield. From 23, the ABCDE pentacyclic skeleton of phainanoids (27) was ultimately established via a Mitsunobu reaction, intramolecular nucleophilic substitution with in situ-generated aryllithium, and protecting group

• room temperature, delivering spiroacetal (S)-114 with complete retention of configuration (>99% ee). The subsequent one-pot acetylation generated (S)-115 in 83% overall yield over three steps from (S)-112. The following functional group manipulations of (S)-115 – including debenzylation/debromination

Halogenated butyrolactones from the biomass-derived synthon levoglucosenone

• Johannes Puschnig,
• Martyn Jevric and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2025, 21, 2297–2301, doi:10.3762/bjoc.21.175

• enamine 9b, which was completely consumed in 6 hours at room temperature. Following acidic hydrolysis of the enamine, a mixture of α-trifluoromethylated ketone diastereomers was obtained, and subsequent epimerization with K2CO3 afforded 19 as a single stereoisomer in 48% yield. The equatorial position of

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

• 100 μM target concentration (1% DMSO). In the case of 7i, 7j, (E)-9a, and (E)-9b, samples were prepared with 50 μM (1% DMSO) and 100 μM (10% DMSO) target concentration, respectively. The plate was then sealed and shaken for 2 hours at room temperature. Each compound was investigated in 3 replicates

• PBS (pH 6.5) in each well to achieve 100 μM target concentration (1% DMSO). These samples were shaken for 1 hour at room temperature then filtered the same way as the kinetic solubility samples to make initial solutions for the PAMPA assay. The artificial membrane was fabricated by dissolving ʟ-α