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

• Ilia A. Pilipenko Mikhail V. Grigoriev Olga Yu. Ozerova Igor A. Litvinov Darya V. Spiridonova Aleksander V. Vasilyev Sergey V. Makarenko Department of Chemistry, Saint-Petersburg State Forest Technical University, Saint-Petersburg 194021, Russia Department of Organic Chemistry, Herzen State

• Pedagogical University of Russia, Saint-Petersburg 191186, Russia A. E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan 420088, Russia Department of Organic Chemistry, Institute of Chemistry, Saint-Petersburg State University, Saint

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

• Haoxiang Wu Xiangbing Qi National Institute of Biological Sciences, Beijing. No. 7, Science Park Road, Zhongguancun Life Science Park, Changping District, 102206 Beijing, China 10.3762/bjoc.22.4 Abstract Arenes and heteroarenes are easily available building blocks in organic chemistry, and

• highlights representative examples that illustrate recent synthetic advances [35][36]. Hydrogenation of monocyclic aromatic rings Hydrogenation of heterocyclic aromatic rings: Despite the widespread application of six-membered aromatic heterocycles in various fields of organic chemistry, reports on their

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

• Dmitry N. Platonov Alexander Yu. Belyy Rinat F. Salikov Kirill S. Erokhin Yury V. Tomilov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Higher School of Economics National Research University, 101000 Moscow

• , include the formation of norcaradienes, dihydroindazoles, a tetracyclodecene and a hydrazonocycloheptatriene derivative. Keywords: azo shift; cascade reactions; cycloheptatriene; relief of antiaromaticity; umpolung; Introduction Reactivity umpolung [1] is a synthetic concept in organic chemistry that

One-pot synthesis of ethylmaltol from maltol

• Immanuel Plangger,
• Marcel Jenny,
• Gregor Plangger and
• Thomas Magauer

Beilstein J. Org. Chem. 2025, 21, 2755–2760, doi:10.3762/bjoc.21.212

• Immanuel Plangger Marcel Jenny Gregor Plangger Thomas Magauer Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80−82, 6020 Innsbruck, Austria Red Bull Central Laboratory, Betriebsgebiet Hängender Stein 1, 6713 Ludesch, Austria Red Bull Service

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

• 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 Vladimir A. Tartakovsky N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow

• electrochemical cell distinguishes electroorganic synthesis from traditional organic chemistry methods. Particular attention is paid to the generation of radical intermediates via the oxidation or reduction of radical precursors [40][41][42][43][44][45][46][47][48][49]. In this regard, the anodic oxidation of

• determination was performed in the Department of Structural Studies of the Zelinsky Institute of Organic Chemistry, Moscow. Funding This work was supported by the Russian Science Foundation (grant no. 24-13-00439).

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

• Gabor Berecz Andras Dancso Maria Tothne Lauritz Lorand Kiss Gyula Simig Balazs Volk Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, P. O. Box 100, H-1475 Budapest, Hungary HUN-REN Research Centre for Natural Sciences, Institute of Organic Chemistry, Stereochemistry Research

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

• organic chemistry, and particularly in the late-stage functionalization of bioactive compounds, drugs, and natural products. This review highlights recent advances in NHC–organophotoredox dual catalysis, focusing on methodology development, mechanistic insights, and reaction scope for synthesizing

• asymmetric reactions and are functional transformations in synthetic organic chemistry. Especially, 1,2,3-triazole-based NHCs are generally more reactive and stronger σ-donors than imidazole or thiazole analogues. Triazolium NHC enhances their ability to stabilize reactive radical intermediates or acyl anion

• Studer et al., which belongs to the class of aryl and heteroaryl electrophilic substitutions and is a highly versatile synthetic transformation in traditional organic chemistry. A highly regioselective dual catalytic approach for the novel acylation of electron-rich benzo-fused arenes or heterocycles 15

Rapid access to the core of malayamycin A by intramolecular dipolar cycloaddition

• Yilin Liu,
• Yuchen Yang,
• Chen Yang,
• Sha-Hua Huang,
• Jian Jin and
• Ran Hong

Beilstein J. Org. Chem. 2025, 21, 2542–2547, doi:10.3762/bjoc.21.196

• Yilin Liu Yuchen Yang Chen Yang Sha-Hua Huang Jian Jin Ran Hong Faculty of Chemical Engineering and Energy Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P.R. China State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy

The intramolecular stabilizing effects of O-benzoyl substituents as a driving force of the acid-promoted pyranoside-into-furanoside rearrangement

• Alexey G. Gerbst,
• Sofya P. Nikogosova,
• Darya A. Rastrepaeva,
• Dmitry A. Argunov,
• Vadim B. Krylov and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2025, 21, 2456–2464, doi:10.3762/bjoc.21.187

• Alexey G. Gerbst Sofya P. Nikogosova Darya A. Rastrepaeva Dmitry A. Argunov Vadim B. Krylov Nikolay E. Nifantiev Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation 10.3762/bjoc

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

• scaffolds. From the standpoint of organic chemistry, it is evident that these compounds can be efficiently converted into a variety of versatile organic intermediates through the application of ring-opening reactions [49][50][51][52]. In addition to the aforementioned useful properties, the current methods

Adaptive experimentation and optimization in organic chemistry

• Artur M. Schweidtmann and
• Philippe Schwaller

Beilstein J. Org. Chem. 2025, 21, 2367–2368, doi:10.3762/bjoc.21.180

• de Lausanne (EPFL), Lausanne, Switzerland National Centre of Competence in Research (NCCR) Catalysis, École Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland 10.3762/bjoc.21.180 The field of organic chemistry is undergoing a remarkable transformation. The convergence of laboratory

• automation and artificial intelligence is creating unprecedented opportunities for accelerating chemical discovery and optimization [1][2]. This thematic issue explores how adaptive experimentation, automation, and human–AI synergy are reshaping organic chemistry research. Several key technological advances

• this field and the exciting opportunities ahead. As methods for adaptive experimentation continue to advance, maintaining focus on effective human–AI collaboration will be crucial for realizing the full potential of these technologies in organic chemistry. This integration of automation, machine

Insoluble methylene-bridged glycoluril dimers as sequestrants for dyes

• Suvenika Perera,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 2302–2314, doi:10.3762/bjoc.21.176

• Organic Chemistry. Conflict of Interest L.I. is co-founder and holds equity in Reversal Therapeutics (National Harbor, Maryland). L.I. holds equity in Clear Scientific (Cambridge, Massachusetts). The other authors declare no competing financial interests.

Enantioselective radical chemistry: a bright future ahead

• Anna C. Renner,
• Sagar S. Thorat,
• Hariharaputhiran Subramanian and
• Mukund P. Sibi

Beilstein J. Org. Chem. 2025, 21, 2283–2296, doi:10.3762/bjoc.21.174

• bengal), affording diversely substituted products [78]. Electrochemical radical reactions The organic chemistry community has witnessed a resurgence of interest in electrochemical methods for organic synthesis [79]. Organic electrochemistry can provide mild reaction conditions, good functional group

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

• Lifen Peng Ting Wang Zhiwen Yuan Bin Li Zilong Tang Xirong Liu Hui Li Guofang Jiang Chunling Zeng Henry N. C. Wong Xiao-Shui Peng Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of

Further elaboration of the stereodivergent approach to chaetominine-type alkaloids: synthesis of the reported structures of aspera chaetominines A and B and revised structure of aspera chaetominine B

• Jin-Fang Lü,
• Jiang-Feng Wu,
• Jian-Liang Ye and
• Pei-Qiang Huang

Beilstein J. Org. Chem. 2025, 21, 2072–2081, doi:10.3762/bjoc.21.162

• aspera chaetominine B. Keywords: epoxidation; selective epimerization; stereodivergent synthesis; structural revision; tandem reaction; Introduction In contemporary organic chemistry, due to the widespread application of modern separation and analytical techniques, the structural elucidation and

• concerns in the field of total synthesis of natural products [10][11][12][13][14][15][16][17][18][19][20], which is not only essential for organic chemistry in its own right, but also crucial for drug discovery and structural revision of natural products. Although more and more diastereomeric and

α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

• Vladyslav O. Honcharov,
• Yana I. Sakhno,
• Olena H. Shvets,
• Vyacheslav E. Saraev,
• Svitlana V. Shishkina,
• Tetyana V. Shcherbakova and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

• Ave., 60, 61072, Kharkiv, Ukraine Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq., 4, 61022, Kharkiv, Ukraine Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Akademika Kukharya Street, 5, 02660, Kyiv, Ukraine 10.3762/bjoc.21.157 Abstract A small

• ; quinoxalinone derivative; Ugi reaction; Introduction Multicomponent reactions are powerful tools in organic chemistry that enable the synthesis of structurally complex and multifunctional compounds from three or more starting materials in a single synthetic step. They are widely used in drug discovery because

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

• of Fundamental Medicine and Biology, Kazan Federal University, Kremlyovskaya Street 18, Kazan, 420008, Russia Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospekt 47, Moscow, 119991, Russia 10.3762/bjoc.21.148 Abstract Organophosphorus compounds are important in

• synthetic organic chemistry and pharmaceutical applications due to their diverse biological activities. In this study, we synthesized three novel glycidyl esters of phosphorus acids 1–3 via the condensation of chlorophosphine oxides or phosphorus oxychloride with glycidol in the presence of a base

• , phosphine oxides, and bisphosphonates, allows for tailored modifications that enhance selectivity, bioavailability, and reduce potential side effects [8][9][10][11][12][13]. This versatility makes them valuable not only as drugs but also as intermediates in synthetic organic chemistry, facilitating access

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

• Michela Marcon Christoph Haag Burkhard Konig Institute of Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany 10.3762/bjoc.21.143 Abstract Approaching the vast, colourful world of photoswitches from a different field of study or as an undergraduate student

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

• promising industrial relevance. Oxidative cleavage of alkenes to yield carbonyl compounds is one of the key transformations in synthetic organic chemistry [41][42]. Over the past two decades, this field has witnessed significant advancements, primarily through the use of organic oxidants and transition

• advanced strategies have been developed for cleavage of alkenes [48][49][50][51]. Owing to the abundance and versatile applications of styrenes in diverse fields of organic chemistry, some strategies have recently been developed for synthesizing 2,4-disubstituted and 4-substituted quinoline derivatives via

Synthesis of chiral cyclohexane-linked bisimidazolines

• Changmeng Xi,
• Qingshan Sun and
• Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1786–1790, doi:10.3762/bjoc.21.140

• Changmeng Xi Qingshan Sun Jiaxi Xu State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People’s Republic of China 10.3762/bjoc.21.140 Abstract Both chiral bisoxazolines and

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• interaction as an alternative to hydrogen bonding and has been widely used as an important supramolecular tool in broad fields such as materials science, crystal engineering, liquid crystals, synthetic organic chemistry and medicinal chemistry [22][23][24][25][26]. Typically, halogen bonding has been

• diverse C–N atropisomeric compounds possessing carboxamide, imide, lactam, sulfonamide, indole, pyrrole, imidazole, carbazole and amine skeletons have been reported by many groups [1][2][3][4][5][6][7][8][9]. C–N atropisomers are attractive compounds from the viewpoint of not only synthetic organic

• chemistry but also medicinal chemistry [10][11][12][13]. For example, 3-(2-bromophenyl)-2-methylquinazolin-4-one (I), which has a high rotational barrier about the N3–Ar bond, is known as mebroqualone possessing GABA agonist activity (Figure 1) [14][15]. Our group has been exploring asymmetric synthesis of

3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

• Somayyeh Kheirjou,
• Jan Riebe,
• Maike Thiele,
• Christoph Wölper and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2025, 21, 1719–1729, doi:10.3762/bjoc.21.134

• Somayyeh Kheirjou Jan Riebe Maike Thiele Christoph Wolper Jochen Niemeyer Faculty of Chemistry (Organic Chemistry) and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, 45141 Essen, Germany Faculty of Chemistry (Inorganic Chemistry), University of Duisburg-Essen

Approaches to stereoselective 1,1'-glycosylation

• Daniele Zucchetta and
• Alla Zamyatina

Beilstein J. Org. Chem. 2025, 21, 1700–1718, doi:10.3762/bjoc.21.133

• Daniele Zucchetta Alla Zamyatina Department of Natural Sciences and Sustainable Resources, Institute of Organic Chemistry, BOKU University, 1190 Vienna, Austria 10.3762/bjoc.21.133 Abstract Nonreducing disaccharides are prevalent in non-mammalian glycans and glycolipids, serving as pivotal

Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade

• Feng Zhou,
• Chuansong Duanmu,
• Yanxing Li,
• Jin Li,
• Haiqing Xu,
• Pan Wang and
• Kai Zhu

Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132

• engaged in the development of continuous-flow nitration systems. Keywords: continuous-flow; kinetics; nitration; optimization; scale up; Introduction Nitro compounds hold an extremely important position in the field of organic chemistry, mainly because they are easily obtainable and can be converted

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

• Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

• become a hot topic in synthetic organic chemistry. Isocyanides (also termed isonitriles) are a class of highly versatile building blocks in organic synthesis, participating in a wide range of transformations including multicomponent reactions (e.g., the well-known Passerini and Ugi reactions) [13][14][15