The trans-influence in gold chemistry from a catalytic perspective

• Manfred Bochmann

Beilstein J. Org. Chem. 2026, 22, 838–856, doi:10.3762/bjoc.22.66

• (II) congener, K[PtCl3(ethylene)] [28], as well as the first examples of gold(III) alkyne [29], CO [30], hydride [31] and σ-complexes [32] (Scheme 3). The olefin complexes were isolated as microcrystalline powders which as dry solids are fairly stable in air at room temperature. The olefin bonding is

• chemical reactivity. For example, 8a proved stable to air, water and acetic acid, although stronger acids like trifluoroacetic lead to decomposition due to protolytic cleavage of one of the Au–phenyl bonds [31][32]. The stabilising effect of the N-donor in C^N^C ligands is seen quite generally and leads to

Knoevenagel condensation of 4,5- and 1,8-diazafluorenes

• Darya S. Cheshkina,
• Christina S. Becker,
• Alina A. Sonina and
• Maxim S. Kazantsev

Beilstein J. Org. Chem. 2026, 22, 803–812, doi:10.3762/bjoc.22.62

• washed sequentially with water, methanol, hexane, then dried in air. General method (A2) for the condensation in other acidic conditions A mixture of diazafluorene (30.0 mg, 0.18 mmol), ammonium acetate (60.5 mg, 0.79 mmol), and aldehyde (0.20 mmol), glacial acetic acid (0.02 mL, 0.36 mmol), ethanol or

• , methanol, hexane, and dried in air. In the case of absence of any precipitate, the solutions were extracted with chloroform, dried over anhydrous MgSO4 and concentrated under reduced pressure. The products were purified either by column chromatography on silica gel (eluent ethyl acetate) or by addition of

• diethyl ether to the residue after evaporation followed by filtration of the resulting precipitate, which was then washed with diethyl ether, and dried in air. General method (B1) for the condensation in basic conditions In a manner analogous to [34]. A solution of diazafluorene (30.0 mg, 0.18 mmol) in

Anti-invasive and cytotoxic evaluation of a (+)-pinoresinol-based semisynthetic library against glioblastoma

• Chen Zhang,
• Kah Yean Lum,
• Jonathan M. White,
• Paul I. Forster,
• Nicholas Booth,
• Sunita A. Ramesh and
• Rohan A. Davis

Beilstein J. Org. Chem. 2026, 22, 691–704, doi:10.3762/bjoc.22.54

• cancer cells from moving. In this study, a unique plant-derived lignan‑based library was screened against glioblastoma (brain cancer) cell lines to evaluate anti-invasive and cytotoxicity effects. Results and Discussion The air-dried and ground seeds of E. maculata were sequentially extracted with CH2Cl2

• biota library housed at the Institute for Biomedicine and Glycomics, Griffith University, Australia. This seed sample was collected on December 3, 1993 at Mount Crosby, Queensland, Australia. A voucher specimen (AQ600324) has been deposited with the Queensland Herbarium. Extraction and isolation The air

Photoorganocatalytic trifluoromethylation of (het)arenes in green conditions

• Egor N. Boronin,
• Svetlana E. Kaurkina,
• Milena M. Svetlakova,
• Anton S. Bolshakov,
• Maxim V. Arsenyev,
• Vasilii F. Otvagin,
• Alexey Yu. Fedorov,
• Timothy Noël and
• Alexander V. Nyuchev

Beilstein J. Org. Chem. 2026, 22, 662–671, doi:10.3762/bjoc.22.50

• protocol [16]. Finally, a series of control experiments was carried out. No product formation was observed in the absence of catalyst (Table 1, entry 11), in the dark (entry 12), in the presence of TEMPO (entry 13), or under an air atmosphere (entry 14). Based on the optimization studies, the standard

• , radical trapping experiments were conducted. In line with the results obtained during the optimization, no product formation was observed in the presence of TEMPO or under air (Table 2, entries 13 and 14). To further probe the mechanism, the reaction mixture from the TEMPO-containing experiment was

Modern synthetic pathways towards eribulin and its subunits

• Sebastian Dominik Graf

Beilstein J. Org. Chem. 2026, 22, 495–526, doi:10.3762/bjoc.22.37

• , 38, 39 (proton sponge), LiCl, Mn, ZrCp2Cl2, MeCN, EtOAc; (b) SrCO3, t-BuOH, H2O, open air; (c) Pd2dba3, PCyp3, CrCl3, NbCpCl4, Zn(0), DMI, THF; PCyp3: tricyclopentylphosphine; DMI: 1,3-dimethyl-2-imidazolidinone. Synthesis of 45. Above: Reaction conditions: (a) methoxyacetic acid, BF3·OEt2, DCM, −30

Recent advances in the stereoselective synthesis of distal biaxially chiral molecules

• Fanxing Zhou,
• Chen Zhang,
• Lingyu Sun,
• Yiyun Fang,
• Siming Zheng,
• Lina Hu,
• Mengyang Shen,
• Zhen Zhao,
• Wei Xu,
• Yunqiang Sun and
• Zi-Qiang Rong

Beilstein J. Org. Chem. 2026, 22, 461–479, doi:10.3762/bjoc.22.34

• axially chiral bridged teraryl molecules 34 (Scheme 9) [50]. This method provided access to biaxial bridged eight-membered terphenyl atropisomers with broad substrate scope, high yields, and operational simplicity under air. In parallel, Shi’s group developed a cobalt-catalyzed asymmetric synthesis of

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

• for 1 h. The delipidated rice bran was filtered through a non-woven filter and dried in air overnight. A 1.0 M HCl solution (300 mL) was poured into the rice bran, and the produced mixture was stirred with a magnetic stirrer for 1 h. After stirring, the pH of the extract was adjusted to 4.5 with 8.0 M

Base-promoted deacylation of 2-acetyl-2,5-dihydrothiophenes and their oxygen-mediated hydroxylation

• Vladimir G. Ilkin,
• Margarita Likhacheva,
• Igor V. Trushkov,
• Tetyana V. Beryozkina,
• Vera S. Berseneva,
• Vladimir T. Abaev,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2026, 22, 192–204, doi:10.3762/bjoc.22.13

• products (Scheme 1D) or the deacetylated products (Scheme 1E) have been developed. Results and Discussion Dihydrothiophene 1a was selected as a model substrate for our optimization study (Table 1). Initially, this compound was treated in ethanolic solution (2 mL) at room temperature in air for 1 h in the

• air this reaction proceeded more selectively, and the pure product 3a was isolated in 78% yield (Table 1, entry 9). Hydroxy-substituted product 2a also formed in solution of iPrOH or n-BuOH, and this product was isolated in 35 or 46% yields, respectively (Table 1, entries 10 and 11). In a solution of

• -dihydrothiophene 2a were found to be the use of 5.0 equiv of sodium in an oxygen saturated ethanolic solution at rt for 1 h. The deacylated product 3a was synthesized in high yield when the reaction was performed with 5.0 equiv of sodium in methanolic solution at rt for 1 h in contact with air. With these optimal

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

• 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

• dissolved in 10 mL of water, containing 6 mmol of HCl). It was stirred at room temperature for 5 h, the solid product obtained was filtered, washed with water (2 × 3 mL), and air-dried. It was dissolved in acetone (20 mL), the solution was treated with charcoal (0.20 g), and evaporated in vacuo. The residue

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

• was filtered and thoroughly washed with DMF, water and methanol in order to remove byproducts and unreacted BU1. After air-drying, SG-NHCO-BU1 was obtained. Preparation of SG-BU1 For the preparation of SG-BU1 with electrostatically bound BU1 on the surface of silica gel, a-SG (0.9 g) was suspended in

• DMF (15 mL) and BU1 (0.1 g), dissolved in a minimum amount of DMF, was added. The dispersion was mechanically shaken (180 rpm) at ambient temperature for 5.5 h. Afterwards, the dispersion was filtered, washed with DMF (5×) and methanol (5×) to remove unattached BU1. After air-drying in a hood

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

• visible region, and improved morphological stability [4][5][6]. Recent reports have shown that the development of alkyl-supported TT-based semiconductors has led to high-performance, air-stable OFETs [7], while integration of TT frameworks into donor–acceptor architectures has enabled the development of

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

• chloroform and toluene do not pose a risk to 3 species (please see the green colored icons). In terms of environmental risk factors, the persistence of methyl laurate in soil, sediment and water, with the exception of air, is significantly lower than that of the other two solvents (values are calculated in

• of hexane and dried in open air. The resulting mixture of isomers was subjected to direct NMR analysis, without any additional purification or separation steps. Versatile compounds via cycloaddition reactions. a) Radar view of the physical properties of methyl laurate. b) Oral toxicity values of

Electrochemical cyclization of alkynes to construct five-membered nitrogen-heterocyclic rings

• Lifen Peng,
• Ting Wang,
• Zhiwen Yuan,
• Bin Li,
• Zilong Tang,
• Xirong Liu,
• Hui Li,
• Guofang Jiang,
• Chunling Zeng,
• Henry N. C. Wong and
• Xiao-Shui Peng

Beilstein J. Org. Chem. 2025, 21, 2173–2201, doi:10.3762/bjoc.21.166

• (0.3 mmol) and n-Bu4NBF4 (0.45 mmol), under electrolysis (Pt plate as electrodes, 5 mA) at air for 10 h. Electron-donating (Me, Et, t-Bu and OMe) or electron-withdrawing (Cl, Br and F) groups involved phenylacetylenes, 1-ethynylnaphthalene and 2-ethynylthiophene were tolerated well under these reaction

C2 to C6 biobased carbonyl platforms for fine chemistry

• Jingjing Jiang,
• Muhammad Noman Haider Tariq,
• Florence Popowycz,
• Yanlong Gu and
• Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

• a C1 building block for the N-formylation of secondary amines to formamides under catalyst-free conditions and air as oxidant. This method was applied to different aromatic and aliphatic (both cyclic and acyclic) amines (Scheme 3) [31]. Already in 1955, Parham and Reiff reported the synthesis and

The application of desymmetric enantioselective reduction of cyclic 1,3-dicarbonyl compounds in the total synthesis of terpenoid and alkaloid natural products

• Dong-Xing Tan and
• Fu-She Han

Beilstein J. Org. Chem. 2025, 21, 2085–2102, doi:10.3762/bjoc.21.164

• and aldehyde 37, which was prepared with 9 steps from commercially available (+)-citronellol, underwent a Reformatsky-type radical addition under the conditions of Et3B/air/Bu3SnH to deliver aldol product [16]. Dehydration of the secondary alcohol gave (E)-38. The HAT radical cyclization [17] of 38 in

Photoswitches beyond azobenzene: a beginner’s guide

• Michela Marcon,
• Christoph Haag and
• Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

• , this form is not stable, and it easily undergoes irreversible oxidation under air to give phenanthrene (IV). This challenge was addressed by substituting the hydrogen atoms with methyl groups in 124-II. Moreover, the E–Z isomerisation could be avoided by adding a ring to the central double bond, thus

Fe-catalyzed efficient synthesis of 2,4- and 4-substituted quinolines via C(sp²)–C(sp²) bond scission of styrenes

• Prafull A. Jagtap,
• Manish M. Petkar,
• Vaishnavi R. Sawant and
• Bhalchandra M. Bhanage

Beilstein J. Org. Chem. 2025, 21, 1799–1807, doi:10.3762/bjoc.21.142

• [53]. In this work, the authors used a stoichiometric amount of Zn(OTf)3 as a Lewis acid catalyst and air as the oxidant for the reaction. Jana and colleagues demonstrated an atom-efficient pseudo-three-component C–H annulation reaction catalyzed by Yb and Cu, which involved nitrosoarenes and styrene

Formal synthesis of a selective estrogen receptor modulator with tetrahydrofluorenone structure using [3 + 2 + 1] cycloaddition of yne-vinylcyclopropanes and CO

• Jing Zhang,
• Guanyu Zhang,
• Hongxi Bai and
• Zhi-Xiang Yu

Beilstein J. Org. Chem. 2025, 21, 1639–1644, doi:10.3762/bjoc.21.127

• target Heck coupling, finding that using 1,4-dioxane as the solvent and 20 mol % PdCl2 as the catalyst, 11 could be obtained in 40% yield in the air. We tried by using more catalyst, or adding O2 (or CuCl2) as oxidant, but all these efforts did not give improved reaction yields (the reason for this was

Facile synthesis of hydantoin/1,2,4-oxadiazoline spiro-compounds via 1,3-dipolar cycloaddition of nitrile oxides to 5-iminohydantoins

• Juliana V. Petrova,
• Varvara T. Tkachenko,
• Victor A. Tafeenko,
• Anna S. Pestretsova,
• Vadim S. Pokrovsky,
• Maxim E. Kukushkin and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 1552–1560, doi:10.3762/bjoc.21.118

• triethylamine solution was slowly added dropwise to the reaction mixture at 0 °C under an inert gas atmosphere to avoid moisture from the air (“classical” method). In another method, the base was inserted via diffusion of NEt3 into a solution containing the dipolarophile and dipole precursor (see Figure S1 in

General method for the synthesis of enaminones via photocatalysis

• Paula Pérez-Ramos,
• Raquel G. Soengas and
• Humberto Rodríguez-Solla

Beilstein J. Org. Chem. 2025, 21, 1535–1543, doi:10.3762/bjoc.21.116

• adduct 10 was identified using GC–MS (Figure S1, Supporting Information File 1). When the reaction was performed under air-equilibrated conditions, the intended product 9a was obtained in a 31% yield, indicating that air influenced the interaction between the Ni-catalyst and the α,β-unsaturated carbonyl

Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones

• Grzegorz Mlostoń,
• Małgorzata Celeda,
• Marcin Palusiak,
• Heinz Heimgartner,
• Marta Denel-Bobrowska and
• Agnieszka B. Olejniczak

Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113

• hours of cooling a colorless solid was separated. The crystalline material was filtered off and dried in the air at rt. 10-Thia-7,8-diazatrispiro[4.0.46.0.411.15]hexadec-7-en-16-one (2c): Yield: 910.0 mg (91%); mp 53‒55 °C (dec.); 1H NMR (CDCl3) δ 1.32–1.39 (m, 2H), 1.39–1.48 (m, 2H), 1.53–1.60 (m, 2H

Highly distinguishable isomeric states of a tripodal arylazopyrazole derivative on graphite through electron/hole-induced switching at ambient conditions

• Himani Malik,
• Sudha Devi,
• Debapriya Gupta,
• Ankit Kumar Gaur,
• Sugumar Venkataramani and
• Thiruvancheril G. Gopakumar

Beilstein J. Org. Chem. 2025, 21, 1496–1507, doi:10.3762/bjoc.21.112

• pyrolytic graphite (HOPG, ZYB grade from μMasch). Approximately 4 μL of solutions of FNAAP were drop-casted on the HOPG surface, dried (a few minutes) in ambient conditions, and AFM/STM studies were performed. Relative humidity (≈50%) and temperature (22–25 °C) of the room were controlled by an air

• green dashed lines. Two resonances are rotated by ≈120° and correspond to the major orientations of the domains in the 1D phase. Constant current STM topographs (300 pA, 0.3 V) of the FNAAP adlayer on HOPG (a, b) deposited from the corresponding ethanolic solution. Imaging is performed at the HOPG–air

Photoredox-catalyzed arylation of isonitriles by diaryliodonium salts towards benzamides

• Nadezhda M. Metalnikova,
• Nikita S. Antonkin,
• Tuan K. Nguyen,
• Natalia S. Soldatova,
• Alexander V. Nyuchev,
• Mikhail A. Kinzhalov and
• Pavel S. Postnikov

Beilstein J. Org. Chem. 2025, 21, 1480–1488, doi:10.3762/bjoc.21.110

• . Finally, control experiments without irradiation gave only traces of the benzamide 2aa showing no activation by the Ru complex at room temperature (Table 1, entry 24). An experiment conducted under an air atmosphere yielded only 9% of 2aa (Table 1, entry 25) indicating that the presence of atmospheric

Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

• Andrei Paraschiv,
• Valentina Maruzzo,
• Filippo Pettazzi,
• Stefano Magliocco,
• Paolo Inaudi,
• Daria Brambilla,
• Gloria Berlier,
• Giancarlo Cravotto and
• Katia Martina

Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108

• being applied when reacting amides to achieve their decarbonylation. In 2014, Cao et al. [47] reported the amination of benzoxazole with a secondary amine either in air or an O2 atmosphere, lowering the catalyst amount and the reaction temperature. In 2020, a study by De Vos and co-workers [48] focused

• temperature and gas pressure (up to 300 °C and 200 bar). The SynthWave reactor also allows multiple gases to be loaded, including both inert and reactive gases. As shown in Table 2, MW irradiation significantly reduced reaction times from 6 hours to 2 hours under atmospheric air conditions. At 60 °C with 20

• 13%, highlighting the importance of oxygen/air in the oxidative aromatisation of the benzoxazole ring. Reducing the reaction time to 1 hour or lowering the catalyst loading to 15 mol % resulted in decreased yields of 75% and 71%, respectively. The reaction was also carried out in Anton Paar equipment

High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters

• Kelsey Plasse,
• Valerie Wright,
• Guoshu Xie,
• R. Bernadett Vlocskó,
• Alexander Lazarev and
• Béla Török

Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102

• instrument is depicted in Figure 1. The core of the instrument is the intensifier which generates the required pressure by amplifying the relatively low pressure (about 140 psi) supplied by an air compressor. The intensifier pressurizes the water in the pressure chamber where the sealed samples are placed

• reaction time. Even the less reactive aniline gave nearly quantitative isolated yields in less than an hour, while the 1 bar control reaction yielded no detectable products. In addition to the excellent yields, the products were isolated without any purification, using a simple air-drying process to remove

• removing the reaction vessel from the pressure chamber, the cap was removed and the solid material was collected and dried by a simple air-drying. After drying 96.92 g of the product was obtained. The purity of the product was determined by an Agilent 7250 GC-QTOF mass spectrometer operated in electron