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

• their broader use. With this in mind, Lee and colleagues have recently developed an efficient synthetic method for producing o-carborane-fused pyrazoles as a novel scaffold, without using transition metals. Their approach involves reacting B(4)-acylmethyl and B(3,5)-diacylmethyl o-carborane with 2-azido

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

• -derived Functional Oligosaccharides Engineering Technology Research Center of Anhui Province, Fuyang Normal University, Fuyang, Anhui, 236037, P. R. China 10.3762/bjoc.21.17 Abstract A new synthetic method for disulfides and 3-sulfenylchromones is reported. This innovative approach is based on the

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

• has emerged as a potential synthetic tool for the formation of new C–C, and C–heteroatom bonds using electricity to replace the stoichiometric amounts of conventional chemical redox reagents [47]. C–C Bond formation In 2019, the Ackermann group established a synthetic method for isoindolones using a

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

• intermediate XXXV. Finally, the final product 35 is yielded via a 1,3-hydride shift. The reaction between diazo derivatives, nitriles, and azodicarboxylates catalyzed by Cu(OTf)2 is an efficient synthetic method to obtain 2,3-dihydro-1,2,4-triazole derivatives 36 (Scheme 27) [45]. The reaction proceeds via a

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• , obtained in 50% yield, opening great possibilities in structural variations. The facile synthesis of G55, G66, and G48 demonstrates again the versatility of this synthetic method. The synthesis and detailed characterization of compounds F6 and G66 have been the subject of a preliminary patent description

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• interactions could fix the rotaxane structure. Such a fundamental systematic study was first possible because of the efficient urea end-capping synthetic method that supported its utility. Notably, other types of rotaxane frameworks have been developed using the pseudo[3]rotaxane-formation or urea end-capping

• species. As these modifications proceeded effectively with high yields (>90%) without any taxing purification by chromatography, a simple filtration-based purification was sufficient. This synthetic method enabled a flexible molecular design of the CD-based rotaxane framework in an easy, scalable manner

C–H Trifluoromethylthiolation of aldehyde hydrazones

• Victor Levet,
• Balu Ramesh,
• Congyang Wang and
• Tatiana Besset

Beilstein J. Org. Chem. 2024, 20, 2883–2890, doi:10.3762/bjoc.20.242

• ). Mechanistic investigations revealed that AgSCF3 was the active species in the transformation. Keywords: C–H bond functionalization; C–S bond formation; hydrazones; synthetic method; trifluoromethylthiolation; Introduction Fluorinated molecules are of paramount importance [1][2][3][4][5][6][7][8][9][10][11

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

• Bhaskar B. Dhotare,
• Seema V. Kanojia,
• Chahna K. Sakhiya,
• Amey Wadawale and
• Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

• very weak estrogenic activity [8]. Although a detailed SAR is still warranted, the initial reports prompted us to find a suitable synthetic method for 5-substituted 2-hydroxybenzopheneones, and to evaluate their UV-absorbing properties. Various methods for the synthesis of benzophenones have been

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

• Haifeng Yu,
• Wanting Zhang,
• Xuejing Cui,
• Zida Liu,
• Xifu Zhang and
• Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

• synthetic method for the preparation of β-keto thioesters and β-keto amides remains imperative. Organic reactions in water are an important and exciting research topic of green chemistry because water as a solvent exhibits fascinating features, such as low cost, good environmental compatibility, nontoxicity

• dithioacetals and nitroethane/amines [72][73]. As part of our continuous research in this context, more recently we investigated the selective hydrolysis of α-oxo ketene N,S-acetals in water to gain an environmentally compliant synthetic method for β-keto thioesters and β-keto amides (Scheme 1c). Herein, we

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

• Akiya Ogawa and
• Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

• understand the conditions for the generation of heteroatom radicals. In addition, from the perspective of recent green chemistry, the development of environmentally friendly synthetic methods is strongly demanded. In other words, a new synthetic method should have excellent atom economy, produce no waste, be

• thermally induced [71]. Radical cyclization of 2-isocyanobiarenes The cycloaddition reaction with 2-isocyanobiaryls 29 under radical conditions is an excellent synthetic method for nitrogen-containing fused heterocycles such as phenanthridine derivatives 31 (Scheme 20) [72][73]. The reaction proceeds by

Cage-like microstructures via sequential Ugi reactions in aqueous emulsions

• Rita S. Alqubelat,
• Yaroslava A. Menzorova and
• Maxim A. Mironov

Beilstein J. Org. Chem. 2024, 20, 2078–2083, doi:10.3762/bjoc.20.179

• colloidosomes is the presence of pores, the sizes of which depend on the parameters of the original colloidal particles and the synthetic method [6]. Pores provide controlled permeability of these structures and open up rich opportunities for practical uses as catalysts, sorbents, and carriers of medicinal

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• of photocatalysts by tuning their redox and photophysical properties. Thus, we successfully developed a one-pot, three-component synthetic method with those substituents in 5-aryldeazaflavins 1 on the deazaisoalloxazine core or on the phenyl ring by condensation of N-substituted anilines, aromatic

Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids

• Sao Sumida,
• Ken Okuno,
• Taiki Mori,
• Yasuaki Furuya and
• Seiji Shirakawa

Beilstein J. Org. Chem. 2024, 20, 1794–1799, doi:10.3762/bjoc.20.158

• were explored to demonstrate the broader applicability of the current synthetic method (Scheme 5). Asymmetric bromolactonization of α,α-diphenyl-5-hexenoic acid (2a), using a chiral bifunctional sulfide catalyst (S)-1g, was scaled up to a 1.0 mmol scale to obtain the optically active bromolactonization

Oxidative hydrolysis of aliphatic bromoalkenes: scope study and reactivity insights

• Amol P. Jadhav and
• Claude Y. Legault

Beilstein J. Org. Chem. 2024, 20, 1286–1291, doi:10.3762/bjoc.20.111

• the regioisomeric mixture of Ritter-type amidation side products 3. Conclusion In summary we have developed a hypervalent iodine-catalyzed synthetic method for the oxidative hydrolysis of diverse dialkyl bromoalkenes. The current approach can tolerate both symmetrical as well as unsymmetrical dialkyl

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• . Conclusion To conclude, we have used an efficient synthetic method to produce a structurally diverse class of H-bonding capable electron-deficient N-heteroacenes DPQDs 1b–7b. The DPQDs were accessed from their respective N-heteroacenes DCPQs 1a–7a in one step. Structure–property relationships for the DCPQs

Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• carbonylative reduction approach of organic nitro compounds has been used for the synthesis of important industrial and pharmaceutical compounds such as indoles. In 1986, Cenini et al. reported a new synthetic method for indoles that involved 2-nitrostyrene derivatives. The reaction took place under drastic

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

• Milandip Karak,
• Cian R. Cloonan,
• Brad R. Baker,
• Rachel V. K. Cochrane and
• Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

• applications due to their improved solubility in aqueous systems. Assembly is achieved by integrating distinct carbohydrate, peptide, and polyprenyl phosphate building blocks. This modular synthetic method allows for the strategic substitution of constituent building blocks at different synthetic stages and

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• been reported involving the use of A3-bilanes [30][31] or dipyrromethane–dicarbinols [32], the modification of A4-porphyrins [33], or the reaction of pyrrole with different aldehydes [34]. In the present work, the applied synthetic method provided the A3B-porphyrins in a single-step reaction from

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• conditions, and allows easy installation of long-chain substituents at the C-2 position of the quinolone core. These characteristics of the synthetic method could be particularly attractive in the search of novel mimics of the Pseudomonas quorum-sensing signal molecules. The high activity of compounds 4d and

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• urgent need to develop diverse monofluoromethylation methods. In this context, Chen and his colleagues recently developed a concise photocatalytic procedure for achieving monofluoromethylation, as well as di- and trifluoromethylation of various alkenes (Scheme 25) [50]. The synthetic method also

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• under basic conditions, and expanded the synthetic method to N-substituted acylhydrazones [106][107] (Scheme 18). In the early development of 1,3-dipolar cycloadditions of azomethine imines, the acyclic azomethine imines were unstable and their in situ preparation required Brønsted acid or thermal

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• properties via an original mechanism of action. The increasing interest in studying ether lipids for fundamental and applied researches invited to review the methodologies developed to prepare ether lipids. In this review we focus on the synthetic method used for the preparation of alkyl ether lipids either

Radical ligand transfer: a general strategy for radical functionalization

• David T. Nemoto Jr,
• Kang-Jie Bian,
• Shih-Chieh Kao and
• Julian G. West

Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90

• report, it augured the potential of RLT to be a general strategy in synthetic method development, with modern examples including new alkene addition reactions and decarboxylative functionalizations (Scheme 2). Recent applications of RLT in catalysis Upon the discovery and initial exploration of the RLT

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

• Alessio Regni,
• Francesca Bartoccini and
• Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

• common synthetic route to ergot alkaloids, providing an advantageous synthetic method for this class of natural products. Further studies on the utility of the decarboxylative radical cyclization and their applications are currently being investigated in our laboratory. (a) Transformations of DMAT to