Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• of the solid products practically impossible. When NMP was used as the solvent, the reaction of 9,10-ANTH(Br)2, BnFI, and Na2S2O3 did not result in the formation of 9,10-ANTH(BnF)2 but mainly in the formation of 9-Br-10-BnF-ANTH (39%, determined by NMR). Overall, the methods described above all

• , whereas 9,10-ANTH(BnF)2 loses vibronic structure in the emission spectrum. This may be the result of different conformations upon relaxation [31]. The HOMO–LUMO gap (Eg) decreases from ANTH (3.28 eV) to 9,10-ANTH(BnF)2 (3.05 eV). A decrease in Eg is regarded as one of the methods for improving the

• reactions) Dry Mg turnings (excess) were added to an oven-dried 100 mL Schlenk flask and mechanically activated via stirring and heating. After 1 h, dry THF (20 mL) and 9,10-ANTH(Br)2 (84 mg, 0.25 mmol) were added. Several activation methods were tried (ultra sonic bath, careful heating, addition of I2

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

• Metodej Dvoracek,
• Brendan Twamley,
• Mathias O. Senge and
• Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

• absorption correction using SADABS was applied [32][33]. Structures were solved by dual methods using SHELXT and refined by full-matrix least-squares methods against F2 by SHELXL using Olex2 [34][35]. All non-hydrogen atoms were refined with anisotropic displacement parameters. All hydrogen atoms were

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• reasonably fast labeling kinetics and up to quantitative conversion under quasi-physiological conditions [4]. Obviously, the rapid dissemination and widespread acceptance of such labeling methods depend on fast and simple access to the small molecule probes. Here, we report efficient synthetic routes to

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• in the reaction mixture [2] and is the most practical method applied in the pharmaceutical industry [3]. However, research in this field has developed new resolution methods known as deracemization [4] and dynamic kinetic resolution (DKR) [5]. Currently, organocatalysis has enabled more efficient

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• photon by a molecule causes the reorganization of the electron density around the atoms and unlocks unique reactivity modes [2][3]. In photochemical methods, light is directly absorbed by a functional group embedded in the substrate and can be exploited for example to cleave bonds or trigger

• solvent. Mechanochemical synthesis, particularly through ball milling, has emerged as a powerful and sustainable technique that offers numerous advantages over traditional solution-phase methods [40][41][42]. By often eliminating the need for solvents, mechanochemistry reduces environmental impact and

• of the current technological advancement in the field. This Perspective is organized into four sections based on the adopted setup for photomechanochemistry: manual grinding, vortex mixing, rod milling methods, and ball milling (Figure 2, bottom). One final note is about the solvent adopted: in some

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

• Yuriy I. Horak,
• Roman Z. Lytvyn,
• Andrii R. Vakhula,
• Yuriy V. Homza,
• Nazariy T. Pokhodylo and
• Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

• [11][12][13]. Advancements in one-pot syntheses, like combining the Ugi reaction with other methods [14][15][16][17][18], for example, the Huisgen cycloaddition, have led to the creation of unique [1,2,3]triazolo[1,5-a]pyrazine derivatives [19]. Tandem reactions are particularly valued for their atom

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

• Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

• catalysis [229]. Methods to study the structural detail of catalysis in frameworks remain limited, and crucial techniques like solution-phase NMR are rarely useful [22]. Enzyme encapsulation [230], and electro- and photocatalysis are known [228], and chiral and low symmetry MOFs are an exciting avenue

• methods in materials discovery are unlikely to discover solution-phase sensors or catalysts without a rational starting point to build from. Instead, new receptors [413] and catalysts [414][415][416] will likely arise from improvements in computational rationalization of experimental data [415][417

• purification possibilities available for robust organic cages mean access to structural families via stepwise synthesis or statistical methods followed by separation is facile, as demonstrated by Otte [42][43][44] and ourselves [41]. The lack of internal functionality in cavities doesn’t just reduce the

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

• Zahra Noori,
• Miquel Solà,
• Clara Viñas,
• Francesc Teixidor and
• Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

• materials [28][29][30]. As a result, developing efficient methods for selectively introducing functional groups into carboranes has become a key area of research [29][31]. Moreover, replacing planar aryl rings in biologically active molecules with spherical carborane units has led to novel alternatives [32

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

• Yurii A. Sayapin,
• Eugeny A. Gusakov,
• Inna O. Tupaeva,
• Alexander D. Dubonosov,
• Igor V. Dorogan,
• Valery V. Tkachev,
• Anna S. Goncharova,
• Gennady V. Shilov,
• Natalia S. Kuznetsova,
• Svetlana Y. Filippova,
• Tatyana A. Krasnikova,
• Yanis A. Boumber,
• Alexey Y. Maksimov,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

• reaction of o-chloranil with benzoannelated derivatives of 2,3,3-trimethylindolenine, a comprehensive evaluation of the structure of the compounds obtained using quantum chemical methods, X-ray diffraction analysis, two-dimensional correlation NMR spectroscopy, as well as investigation of their ionochromic

• 1,2-benzoquinone and o-chloroanil, respectively [1][25]. The structures of compounds 7 and 8 obtained by methods A and B were confirmed by 1H NMR, IR spectroscopy and mass spectrometry (Supporting Information File 2). A distinctive feature of the 1H NMR spectra of 7 in CDCl3 is the signal of the

• -ray diffraction analysis. Using two-dimensional correlation NMR spectroscopy methods, it was shown that the nature of the solvent significantly affects the equilibrium of the tautomeric forms of the 1,3-tropolones. The obtained compounds represent molecular switches of optical and fluorescent

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• resistance [2]. Innovative scaffolds for novel antibiotic drug candidates are required to create new methods for safe and effective treatments. Chemically designed drug leads can complement naturally found antibiotics and may engage multiple modes of action and might have a longer lifetime before resistance

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

• of the synthesized compounds were proven by a set of physicochemical methods, including X-ray diffraction analysis. Keywords: CH-acids; 1-halo-1-nitroethenes; heterocyclization; nitroacrylates; X-ray diffraction analysis; Introduction The combination of the furan ring with various carbo- and

• ]. 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

• case of 2e) or alcohol (in the case of 2f,g) solution for 1–3 h (ratio of acrylate/CH-acid/AcOK = 1:1:1.5) with a yield of 43–64% (Scheme 7). The structures of the obtained condensed furans 3–7 were characterized by a set of physicochemical methods, including X-ray diffraction analysis. Analysis of the

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• experimental methods Optical rotations at 20 °C were measured with an Anton Paar MCP 150 circular polarimeter (Anton Paar, Graz, Austria). UV–vis spectra spanning the 190–600 nm range were acquired using a Shimadzu UV2450 spectrophotometer (Shimadzu, Kyoto, Japan). Electronic circular dichroism (ECD) spectra

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• therapeutic methods [78][79][80]. Such reactions can be performed at particular locations such as DNA or tubulin, when the photocatalyst is placed via a tethered ligand (Scheme 17) [81]. In the present case, the triarylmethine dye 67 was used as sensitizer. It is in equilibrium with the lactone form 68 and

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

• Zi-Ying Xiao,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2025, 21, 286–295, doi:10.3762/bjoc.21.21

• and were fully characterized via various spectroscopy methods. The further annulation reaction did not proceed under the reaction conditions. The similar reaction of triphenylphosphine and MBH maleimides of isatins also resulted in the corresponding triphenylphosphaneylidenes 6e and 6f in satisfactory

Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity

• Abel Cárdenas,
• Zexin Jin,
• Yong Ni,
• Jishan Wu,
• Yan Xia,
• Francisco Javier Ramírez and
• Juan Casado

Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20

• , 2000 scans at a resolution better than 4 cm−1 were accumulated to optimize the signal-to-noise ratio. Theoretical methods Quantum chemistry was addressed with the Gaussian 09 suite of programs [28]. DFT calculations were performed at the (U)B3LYP[29][30] level, using the 6-311G* basis set [31]. This

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

• Islam S. Marae,
• Jingyun Tan,
• Rengo Yoshioka,
• Zakaria Ziadi,
• Eugene Khaskin,
• Serhii Vasylevskyi,
• Ryota Kabe,
• Xiushang Xu and
• Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

• of zigzag and armchair edges, which may serve as a key building block for obtaining multifunctional organic materials [7]. Since the initial synthesis of BPP by Scholl and Neumann [8], simplified synthetic methods for BPP have been reported over the past decades [9][10][11][12][13][14]. Recently, a

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

• Dmitry E. Shybanov,
• Maxim E. Kukushkin,
• Eugene V. Babaev,
• Nikolai V. Zyk and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

• due to the addition of another equivalent of active methylene compound were also observed. Among the reactions studied, the diffusion mixing method gave the highest yield when using Meldrum’s acid as CH acid and in reactions with cyclopentadiene as diene. Experimental Materials and methods All

• solvents used were purified and dehydrated using the methods described in reference [28]. All starting reagents were purchased from commercial sources (e.g., Sigma-Aldrich, abcr, AKSci). Reactions were checked by TLC analysis using silica plates with a fluorescent indicator (254 nm) and visualized with a

Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI

• Zhenlei Zhang,
• Ying Wang,
• Xingxing Pan,
• Manqi Zhang,
• Wei Zhao,
• Meng Li and
• Hao Zhang

Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17

• tetrabutylammonium iodide (TBAI)/H2SO4 reduction system using sodium sulfinate as key component, thus eliminating the need for thiols and redox reagents commonly used in traditional methods. Various disulfides and 3-sulfenylchromones were obtained in moderate to excellent yields through this methodology. Mechanistic

• antibody–drug coupling (ADCs), in which the active drug released in the target cell by selectively breaking the disulfide bond [11]. Given the wide applicability of disulfides, the development of efficient, green, mild, and cost-effective methods for the organic synthesis of disulfides is of significant

• catalysts in conjunction with oxygen [17][18][19][20][21][22], electrochemical oxidation [23][24], and photochemical oxidation techniques [25] have emerged as alternative methods. However, these approaches have a significant limitation: the substrates must be thiols, which have unpleasant odors. This has

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

• Misato Suganuma,
• Daichi Kitagawa,
• Shota Hamatani and
• Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

• effective methods for predicting the thermal back reactivity, density functional theory (DFT) calculations can be considered [51][58][59][60][61][62]. For example, in previous studies on the thermal back reactivity of diarylbenzene that is an analogue of diarylethene, we found that the M06-2X level of

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

• Yujun Pang,
• Jinglan Yan,
• Nawaf Al-Maharik,
• Qian Zhang,
• Zeguo Fang and
• Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

• designed with a PhCF2 group (Figure 1a) [8][9][10]. As a result, there is a pressing need for the development of efficient methods for incorporating both the CF2H and PhCF2 groups into diverse molecular frameworks, particularly those with bioactivity properties. The benzimidazole core is widely recognized

• −), respectively (Scheme 1a). Despite these advances, the above methods still suffer from several limitations, including a narrow substrate scope, the reliance on expensive metal catalysts and excess additives, and the need for multistep synthesis of difluoromethylating reagents. These drawbacks restrict their

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• such, it is becoming increasingly essential for synthetic methods to align with a net-zero carbon future [2][3]. Therefore, advancing C1 chemistry remains a crucial endeavor for our group [4]. In synthetic organic chemistry, C1 compounds are usually installed using CO, CO2, HCO2H, CH3OH and CH4, which

• methods, synthetic procedures, analytical data and exemplary copies of NMR spectra of novel compounds. Supporting Information File 97: CheckCIF report for 7b. Supporting Information File 98: CIF file for 7b. Acknowledgements We acknowledge the mass spectrometry facility of the University of Crete

Quantifying the ability of the CF₂H group as a hydrogen bond donor

• Matthew E. Paolella,
• Daniel S. Honeycutt,
• Bradley M. Lipka,
• Jacob M. Goldberg and
• Fang Wang

Beilstein J. Org. Chem. 2025, 21, 189–199, doi:10.3762/bjoc.21.11

• established methods, including 1H NMR-based hydrogen bond acidity determination, UV–vis spectroscopy titration with Reichardt's dye, and 1H NMR titration using tri-n-butylphosphine oxide as a hydrogen bond acceptor. Our experiments reveal that the direct attachment of the CF2H group to cationic aromatic

• assigning specific contributions of each to the observed binding affinities. Even so, 1H NMR titration experiments with phosphine oxides still allow us to partially resolve these two forces by monitoring the proton of the CF2H group. Such issues are particularly salient when quantification methods that rely

• measurements is desirable. Conclusion In conclusion, we have identified a series of CF2H-containing compounds that can serve as HB donors. We employed several experimental methods to quantify HB donation ability, including (i) 1H NMR chemical shift-based hydrogen bond acidity, A value, measurements, (ii) UV

Recent advances in electrochemical copper catalysis for modern organic synthesis

• Yemin Kim and
• Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

• sustainable chemistry, the combination of copper catalysis and electrochemistry is particularly attractive for overcoming challenges associated with conventional methods, and it has led to extensive research in recent years. In this review, we highlight the unique contributions of electrochemical copper

• bromine radical attack that leads to the formation of a cationic brominated copper complex 77. Anodic oxidation and subsequent proton transfer provide the desired product 73 and regenerate the copper catalyst. Olefin addition Hydrofunctionalization and difunctionalization of alkenes are valuable methods

• as a redox mediator with non-copper electrodes (Figure 19) [80]. In the absence of chemical oxidants, this Chan–Lam coupling method resulted in shorter reaction times than those of traditional methods and offered alternative substrate reactivity. This reaction was successfully applied to aryl- and

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

• approach to complex molecule synthesis. Despite considerable efforts to develop various catalytic systems, the activation of aromatic C–F bonds often requires high temperatures [1][2][3][4][5][6][7]. Therefore, methods for activating aromatic C–F bonds at ambient temperature remain underdeveloped. We have

• developed efficient metal-mediated methods for activating (i) vinylic [8][9][10][11][12][13] and (ii) allylic C–F bonds [14][15][16][17][18] using β-fluorine elimination under mild conditions. In these studies, (i) we discovered zirconium-mediated β-fluorine elimination from zirconacyclopropanes A, which