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

• entry 2 versus entry 6 in Table 2). Furthermore, we studied the effect of using an organic acid as the co-catalyst for forming the enamine intermediate from 1 and for the retro-Michael reaction. We observed that benzoic acid (BA) as a co-catalyst provides a lower er than that achieved with PNBA as a co

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

• Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy 10.3762/bjoc.21.33 Abstract Photomechanochemistry, i.e., the merger of light energy and mechanical forces, is emerging as a new trend in organic synthesis, enabling unique reactivities of fleeting excited states under solvent

• research. Keywords: light-mediated synthesis; mechanochemistry; photomechanochemistry; Introduction Light-mediated synthetic methodologies have significantly transformed contemporary organic chemistry by enabling a broad array of previously unattainable transformations [1]. In fact, the absorption of a

• rearrangements. Most organic molecules are colorless and, in fact, do not absorb visible light: highly energetic UV irradiation is typically needed. A milder approach is offered by photocatalytic approaches. Here, a photocatalyst is added to the reaction mixture to convert light energy into chemical potential to

Electrochemical synthesis of cyclic biaryl λ³-bromanes from 2,2’-dibromobiphenyls

• Andrejs Savkins and
• Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

• Andrejs Savkins Igors Sokolovs Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia Faculty of Medicine and Life Sciences, University of Latvia, Jelgavas 1, 1004 Riga, Latvia 10.3762/bjoc.21.32 Abstract The remarkable nucleofugality of bromoarenes in diarylbromonium species

• Belyakov from the Latvian Institute of Organic Synthesis (LIOS) for X-ray crystallographic analysis. We also thank Prof. Edgars Suna (LIOS) for helpful discussions and assistance in preparing the manuscript. Funding This work was financially supported by Latvian Science Council grant LZP-2021/1-0595.

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

• Yuriy I. Horak Roman Z. Lytvyn Andrii R. Vakhula Yuriy V. Homza Nazariy T. Pokhodylo Mykola D. Obushak Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine 10.3762/bjoc.21.31 Abstract A new tandem sequence involving the Ugi

• environmentally friendly synthetic strategies, especially one-pot multicomponent and tandem reactions, are key to modern organic and medicinal chemistry [1][2][3][4][5][6][7] and have proven to be successful in generating diverse heterocyclic scaffolds, as highlighted in a recent book [8]. Multicomponent

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

• demonstrating enzyme-like rate accelerations remain rare. This perspective will briefly highlight some of the key advances in traditional cavity catalysis, by cavity type, in order to contextualize the recent development of robust organic cage catalysts, which can exploit stability, functionality, and reduced

• symmetry to enable promising catalytic modes. Keywords: cavity confinement catalysis; enzyme mimicry; robust organic cages; self-assembly; supramolecular catalysis; Introduction I frequently introduce my research on organic cage enzyme mimics with the following observation. For hundreds of years

• that an underexplored cavity type, robust organic cages [38][39][40][41][42][43][44][45][46][47], are uniquely positioned to facilitate these advances. Outline and Overview The aim of this perspective is twofold: (1) to briefly review the state of the art of cavity catalysis, highlighting the catalytic

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

• pathway through an associative transition state to form the equatorial glycoside, 7. Surprisingly, recent evidences show that typical homogeneous glycosylation reactions in organic solution shift more towards the SN2 end of the mechanistic spectrum [32][33][34], with some exceptions [35]. The kinetic

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

• Research Centre the Southern Scientific Centre of the Russian Academy of Sciences, Rostov-on-Don 344006, Russian Federation Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don 344090, Russian Federation Federal Research Center of Problems of Chemical Physics and Medical

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

• Kirill A. Gomonov Vasilii V. Pelipko Igor A. Litvinov Ilya A. Pilipenko Anna M. Stepanova Nikolai A. Lapatin Ruslan I. Baichurin Sergei V. Makarenko Department of organic chemistry, Herzen State Pedagogical University of Russia, nab. r. Moiki 48, 191186 St. Petersburg, Russian Federation Federal

• Research Center "Kazan Scientific Center of the Russian Academy of Sciences", Arbuzov Institute of Organic and Physical Chemistry, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation 10.3762/bjoc.21.24 Abstract New representatives of dioxodihydronaphtho[2,3-b]furan-, furo[3,2-c][1]benzopyran-, furo[2,3

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

• evaporation at 40 °C, forming a semi-solid residue dispersed in water. Liquid–liquid extraction against EtOAc (1:1) was conducted twice. The organic phases were combined, filtered, and evaporated under vacuum, while the aqueous phase was discarded. Isolation of compounds 1–6 The obtained organic crude extract

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

• , red-light photocatalysis enables innovative applications in phototherapy and controlled drug release, exploiting its tissue penetration and low cytotoxicity. Together, these developments underscore the versatility and impact of red-light photocatalysis, positioning it as a cornerstone of green organic

• chemistry with significant potential in synthetic and biomedical fields. Keywords: green chemistry; medicinal chemistry; organic photochemistry; photocatalysis; red-light mediated transformations; Introduction Red-light-activated photocatalysis has recently gained significant interest as a tool for

• organic photocatalysts. Unlike metal-based systems, organic photocatalysts such as phthalocyanins, squaraines and cyanins, offer effective electron and energy transfer under red-light irradiation without relying on transition metals. This shift towards organic catalysts opens new possibilities for

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

• an indole motif with a ketone and a γ-lactam moiety occur in numerous natural substances [1][2][3][4]. Isatins have many interesting aspects in organic reactions and potential applications. The versatile reactivity of isatins used both as an electrophiles and nucleophiles and their easy availability

• have made them to become valuable building blocks in organic synthesis. Nucleophilic additions or spiroannulation of the highly reactive carbonyl group at the C-3 position of isatins have various fascinating applications in organic synthesis, which allowed transformation of isatins into various

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

• , National University of Singapore, 3 Science Drive 3, Singapore, Singapore 10.3762/bjoc.21.20 Abstract Oxidized states of polycyclic aromatic hydrocarbons are of importance as they represent charged conductive species in organic semiconductor substrates. In this work, we investigated the properties of

• attracted a growing interest in recent times, both from fundamental and technological reasons [9][10][11]. Antiaromaticity destabilizes the ground state of organic molecules by raising their highest energy occupied molecular orbitals, thus allowing for easy oxidation, doping, and electron-transfer reactions

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

• Islam S. Marae Jingyun Tan Rengo Yoshioka Zakaria Ziadi Eugene Khaskin Serhii Vasylevskyi Ryota Kabe Xiushang Xu Akimitsu Narita Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa 904-0495, Japan

• Organic Optoelectronics Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa 904-0495, Japan Science and Technology Group, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa 904

• 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

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

• groups in organic synthesis [1][2][3][4]. In chemistry and biology, disulfide bonds play crucial roles in protein folding and stabilization [5][6][7][8] and in the rubber industry, they are used to link different polymer chains [9][10]. The disulfide bond backbone is commonly used as a linker for

• 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

• sulfinate (Scheme 1) [29][30][31][32]. Among the available alternatives, sodium sulfinate is particularly interesting because it is more stable and easier to transport, and it is widely used in organic synthesis [33][34][35][36][37]. When using sodium sulfite as the starting material for the construction of

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

• of aliphatic and aromatic substituents (Scheme 4). Pyrimidines and pyrimidone-bearing indole derivatives are crucial in organic chemistry because of their extensive use as bioactive compounds with a wide array of significant biological activities (DB03074, DB03304, DB08131) [70][71][72]. In a similar

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

• Seungmin Lee,
• Minsuk Kim,
• Hyewon Han and
• Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

• increasing interest as affordable, versatile, and sustainable catalytic systems. These catalysts are extensively employed in organic synthesis owing to their cost-effectiveness, reduced toxicity, and natural abundance [20][21][22][23][24][25][26][27][28]. The use of copper salts has enabled a variety of

• -phosphorylation of dioxazolones using organic phosphines and copper catalysts [91]. As shown in Scheme 6, a variety of dioxazolones 14 were explored for the synthesis of N-acyl iminophosphoranes 16. Dioxazolones containing aryl and heteroaryl groups were successfully transformed into the desired products in high

• to yield the stable intermediate INT-21. This intermediate releases the N-acyl iminophosphorane 16 through the incorporation of another organic phosphine, thereby regenerating the active copper species 17. 1.6 Synthesis of N-sulfenamides In 2022, the research groups of Wang and Chen introduced a

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

• studies of organic salts in CDCl3, including 1b and 3b, did not produce observable signals. To solubilize the salts better, we substituted deuterated nitromethane (CD3NO2) for CDCl3. Because of the nearly identical hydrogen donation and acceptance abilities of nitromethane (α = 0.22 and β = 0.06

• , the ΔδDMSO–CD3NO2 values of N-methylated CF2H-containing organic salts are generally smaller than those of the corresponding neutral precursors. This observation contradicts our initial prediction that introducing a quaternary nitrogen would enhance the HB donation ability of the CF2H group. It is

Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

• Wentao Yu,
• Zhiyao Yang,
• Chengkan Yu,
• Xiaowei Li and
• Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

• ]. This is not only due to their rich host–guest chemistry but also due to π-surface-enabled self-assembly that enables the creation of various supramolecular structures, such as discotic liquid crystals [33], nanodimers [34], and organic frameworks [35]. Among them, shape-persistent hydrogen-bonded

• amide macrocycle with six aromatic residues (hereafter called cyclo[6]aramide for brevity, Scheme 1a) could mediate dimerization as a host. That is because such a 2D macrocycle has six carbonyl oxygen atoms pointing inwards as binding sites, demonstrating excellent affinity for cationic organic guests

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

• Yemin Kim Won Jun Jang Department of Chemistry and Nanoscience, Ewha Womans University, Seoul, 03760, Korea 10.3762/bjoc.21.9 Abstract In recent decades, organic electrosynthesis has emerged as a practical, sustainable, and efficient approach that facilitates valuable transformations in synthetic

• electrochemistry and copper catalysis for various organic transformations. Keywords: copper; electrochemistry; radical chemistry; single-electron transfer; sustainable catalysis; Introduction Transition-metal-catalyzed cross-coupling has emerged as an effective method for forming carbon–carbon (C–C) and carbon

• –heteroatom (C–X, where X = N, O, or halogens) bonds in organic synthesis. Copper was one of the first transition metals employed in cross-coupling to form C–C and C–X bonds [1][2]. In 1901, Ullmann reported the first cross-coupling reaction for the formation of biaryl compounds in the presence of

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

• organic chemistry owing to their high bond dissociation energy compared to other aromatic C–X (X = Cl, Br, I) bonds [1][2][3][4][5][6][7]. This activation is essential for the late-stage functionalization of stable C–F bonds in complex molecules with reactive functional groups, providing an orthogonal

• mmol), and K2CO3 (50 mg, 0.36 mmol) were added toluene (3.0 mL) and H2O (0.6 mL). After stirring at room temperature for 13 h, the reaction mixture was diluted with H2O. Organic materials were extracted with diethyl ether three times. The combined extracts were washed with brine and dried over Na2SO4

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

• ; heteropolycycles; multicomponent reactions; one-pot reaction; Introduction Copper has gained a relevant role in organic synthesis as an alternative to precious metals due to its low toxicity, ease of handling, high catalytic activity, and cost-effectiveness [1][2]. In recent years, Cu(OTf)2 has significantly

• known processes, a particular Mannich-type reaction was realized in water in the presence of a dendritic 2,2’-bipyridine ligand 2 and Cu(OTf)2 (Scheme 2) [16]. The hydrophobic ligand surrounding the metal revealed to be essential for the organic synthesis in water, thus increasing the reaction yields

Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

• Henrich Szabados Radovan Sebesta Department of Organic Chemistry, Faculty of Natural Science, Comenius University Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia 10.3762/bjoc.21.6 Abstract Axial chirality is present in a variety of naturally occurring compounds, and is

• ; Introduction Stereoselective catalytic formation of chiral compounds is one of the critical tasks of modern organic synthesis [1]. The catalytic formation of compounds with a center of chirality has been the focus of countless works and can now be considered a matured area. On the other hand, the generation of

Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis

• Remi Peters,
• Levy A. Charleston,
• Karinan van Eck,
• Teun van Berlo and
• Daniela A. Wilson

Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5

• room temperature with an organic solvent content of 33% The window for shape transformation seems to lie between 60 °C and 80 °C, with the best result being obtained at 70 °C (Figure 3). When the temperature is too low, the shape transformation cannot happen as the membrane is still too permeable

Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride

• Laura D’Andrea and
• Simon Jademyr

Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4

• NaOH (10 mL) was added under stirring. The mixture was extracted with 2-PrOH (3 × 10 mL), and the organic extracts were combined, thoroughly dried over MgSO4, and filtered. (I): The residue was concentrated under reduced pressure and dissolved in a large amount of diethyl ether. The amino products were

• DCM (3 × 15 mL). The organic extracts were combined, dried over MgSO4, and concentrated under reduced pressure to deliver 9b as colorless liquid (92%). 1H NMR (400 MHz, CDCl3) δ 1.87 (br, 1H), 4.69 (s, 2H), 7.31 (m, J = 2.67 Hz, 1H), 7.37 (m, J = 2.30 Hz, 4H); 13C NMR (151 MHz, CDCl3) δ 65.48, 127.12

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

• reactors; data processing; high-throughput experimentation; machine learning; reaction optimization; Introduction Organic synthesis plays a crucial role in drug discovery, polymer synthesis, materials science, agrochemicals, and specialty chemicals. Their synthesis and process optimization require

• tasks and reducing the overall process development lead time [3][4]. A standard workflow and general methodology for organic reaction optimization through ML methods is shown in Figure 1. The workflow comprises (i) careful design of experiments (DOE); (ii) reaction execution with commercial high

• of suggested optimization results. Through an examination of methodologies, algorithms, and various case studies, this article offers our perspective on the state-of-the-art techniques for optimizing the synthesis of organic molecules, highlighting both challenges and prospects. The structure of this