Catalytic enantioselective synthesis of selenium-containing atropisomers via C–Se bond formations

• Qi-Sen Gao,
• Zheng-Wei Wei and
• Zhi-Min Chen

Beilstein J. Org. Chem. 2025, 21, 2447–2455, doi:10.3762/bjoc.21.186

• formation proceeded through an SN2-type nucleophilic substitution mechanism (Scheme 1). In 2025, Li and co-workers reported a highly efficient rhodium-catalyzed enantioselective C–H selenylation reaction of 1-arylisoquinolines with diselenides, employing 3,5-(CF3)2C6H3CO₂Ag and AgSbF6 as additives [19

Pd-catalyzed dehydrogenative arylation of arylhydrazines to access non-symmetric azobenzenes, including tetra-ortho derivatives

• Loris Geminiani,
• Kathrin Junge,
• Matthias Beller and
• Jean-François Soulé

Beilstein J. Org. Chem. 2025, 21, 2234–2242, doi:10.3762/bjoc.21.170

• were consumed, various impurities, including biphenyls, diarylamines, aniline, and toluidine, were formed in varying amounts. Since a final dehydrogenation step is required to complete the reaction, the experiment was repeated with various oxidants tested as additives. The use of di-tert-butyl peroxide

Thiadiazino-indole, thiadiazino-carbazole and benzothiadiazino-carbazole dioxides: synthesis, physicochemical and early ADME characterization of representatives of new tri-, tetra- and pentacyclic ring systems and their intermediates

• Gyöngyvér Pusztai,
• László Poszávácz,
• Anna Vincze,
• András Marton,
• Ahmed Qasim Abdulhussein,
• Judit Halász,
• András Dancsó,
• Gyula Simig,
• György Tibor Balogh and
• Balázs Volk

Beilstein J. Org. Chem. 2025, 21, 2220–2233, doi:10.3762/bjoc.21.169

• (cpKa values can be found in Table 2). The same analytical method was used with modified eluents: eluent A was 20 mM triethylamine with phosphoric acid (pH 7.0), and eluent B was acetonitrile without additives. The method time was slightly extended, with a 1-minute longer gradient, resulting in an 8

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

• bicyclic alkanes, used as fuel additives, by hydrodeoxygenation catalyzed by iridium/rhenium oxide supported on silica [182]. Conversion of furfural to amines: The synthesis of m-xylylenediamine from furfural and acrylonitrile through a Diels–Alder/aromatization sequence was developed by Wischet and Jérôme

• hydrolysis (Scheme 59). Furfural was employed as starting scaffold in a protocol developed to form acetals as fuel additives. The acyclic acetal is generated in situ from crude furfural with propanol in dimethyl carbonate using a nanoporous aluminosilicate material Al-13-(3.18) as catalyst, and then

• or jet fuel additives through aldol condensation/hydrogenation sequences. The acyclic or cyclic chain hydrocarbons can be formed under hydrodeoxygenation conditions after aldol extension of the C–C chain. Dimers and trimers can be obtained from CPN by self-condensation and converted to C10 and C15

Photochemical reduction of acylimidazolium salts

• Michael Jakob,
• Nick Bechler,
• Hassan Abdelwahab,
• Fabian Weber,
• Janos Wasternack,
• Leonardo Kleebauer,
• Jan P. Götze and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

• an O-benzoylated intermediate species also being obtained under some conditions. Supported by TD-DFT studies, plausible reaction mechanisms for both processes were proposed. Moreover, further investigations employing silicon-containing additives allowed for an increase in the reduction yield beyond

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

• transformation under the given reaction conditions (Table 1, entry 9). The effect of additives on this transformation was then investigated, and it was found that utilizing AcOH and TsOH additives instead of TFA failed to reach optimal yields (Table 1, entries 10 and 11). A noticeable decrease in yield was

Calcium waste as a catalyst in the transesterification for demanding esters: scalability perspective

• Anton N. Potorochenko and
• Konstantin S. Rodygin

Beilstein J. Org. Chem. 2025, 21, 1520–1527, doi:10.3762/bjoc.21.114

• ][4][5][6][7]. Nowadays, esters have found indispensable applications as solvents [8][9][10][11], biolubricants [12][13][14][15], food additives [16][17][18][19], polyester plastics and materials [20][21][22][23][24][25], in the pharmaceutical industry [26][27][28][29][30], in perfumes and flavoring

Copper catalysis: a constantly evolving field

• Elena Fernández and
• Jaesook Yun

Beilstein J. Org. Chem. 2025, 21, 1477–1479, doi:10.3762/bjoc.21.109

• -workers demonstrates that the efficient and green direct C–H amination of benzoxazoles can be catalyzed by copper chloride salts in acetonitrile in the absence of any acidic, basic, or oxidizing additives [8]. Both CuCl and CuCl2 were found to be extremely efficient in promoting the reactions, which

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

• offers wide-ranging potential for substrate expansion and the functionalisation of bioactive compounds. This study presents a green and efficient C–H amination, catalysed by CuCl and CuCl2, in acetonitrile without acidic, basic or oxidant additives that is accelerated by microwave (MW) irradiation and is

• to identify mild conditions for the Cu-catalysed aerobic C–H amination in absence of acid, base or co-catalyst additives. As described in Table 1, we explored the effects of different solvents and copper species, and preliminary reactions were conducted with Cu(II) salts, with reference to reaction

• efficiently, affording good-to-excellent yields. The Boc-protecting group proved to be stable under the reaction conditions, underlining the importance of avoiding the addition of acidic additives. Steric hindrance exerted a moderate influence on the reaction, and branched aliphatic amines yielded the

Oxetanes: formation, reactivity and total syntheses of natural products

• Peter Gabko,
• Martin Kalník and
• Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

• promoted by visible light at room temperature, requires no protecting atmosphere or additives, and the resulting polysubstituted oxetanes are obtained in moderate to good yields. Additional advantages include scalability and high chemoselectivity as various functional groups were tolerated, including

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

• Jiangfei Chen,
• Yi-Lin Qu,
• Ming Yuan,
• Xiang-Mei Wu,
• Heng-Pei Jiang,
• Ying Fu and
• Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

• final products 26k and 26l in 73% and 53% yield, respectively. Radical-trapping experiments with TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) and BHT (butylated hydroxytoluene) additives confirmed the involvement of α-aminoalkyl radicals in this transformation, as shown in Scheme 14. A single-electron

• particularly noteworthy for its use at room temperature, requiring no transition metals, photocatalysts, or additives. Notably, Umemoto's reagent served as the trifluoromethyl source, and the reaction was facilitated under blue LED irradiation, achieving good to excellent yields. Moreover, this approach

Gold extraction at the molecular level using α- and β-cyclodextrins

• Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

• the gold-precipitating properties of a more affordable cyclodextrin, β-CD, is, on the other hand, still taking its first steps. In the case of the bromoaurate ion, the method implies the use of a precipitate co-former. There are, nonetheless, advantages to the use of additives, namely the possibility

• . C skyblue, O red, Br brown, Au yellow. (c) Schematic illustration of the mechanism leading to precipitation (named “supramolecular polymerisation” by the authors) after adding various additives to the solution of β-CD and [AuBr4]− anions. Reproduced from [51] (© 2023 H. Wu et al., published by

Recent advances in controllable/divergent synthesis

• Jilei Cao,
• Leiyang Bai and
• Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

• features of the starting material. By exploiting preorganization, steric effects, or directing groups within the substrate, chemists can achieve high levels of regioselectivity, diastereoselectivity, and enantioselectivity without relying on external catalysts or additives. This approach has been

Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions

• Wen-Hui Mi,
• Teng-Yu Huang,
• Xu-Dong Wang,
• Yu-Fei Ao,
• Qi-Qiang Wang and
• De-Xian Wang

Beilstein J. Org. Chem. 2025, 21, 884–889, doi:10.3762/bjoc.21.72

• ]. Additionally, dicarboxylates like tartrate, adipate or citrate are widely used as food additives [23][24]. Furthermore, functional materials based on dicarboxylates are expected to play a significant role in future technologies [25]. Therefore, the recognition and detection of dicarboxylates are of great

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

• Xuhong Zhao,
• Weishuang Li,
• Mengli Yang,
• Bojie Li,
• Yaoyao Zhang,
• Lizhen Huang and
• Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

• promote this cascade reaction for the synthesis of quinazolinones without the need for additional ligands or additives (Scheme 1a) [7][10]. Since then, various copper-based catalysts, both homogeneous and heterogeneous, have been explored (Scheme 1b) [11][12][13][14][15][16]. For example, Wang’s group

Development and mechanistic studies of calcium–BINOL phosphate-catalyzed hydrocyanation of hydrazones

• Carola Tortora,
• Christian A. Fischer,
• Sascha Kohlbauer,
• Alexandru Zamfir,
• Gerd M. Ballmann,
• Jürgen Pahl,
• Sjoerd Harder and
• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2025, 21, 755–765, doi:10.3762/bjoc.21.59

• industrial production (Table 2, entries 4, 8, and 9). All these experiments gave only low ee values (4–19% ee, Table 2, entries 4–9), with a preference for the S-enantiomer. Use of aromatic alcohol or (R)-1-phenylethanol as additives did not improve either yields or enantioselectivities (Table 2, entries 5

• and 6 vs entry 4). Accordingly, experiments without additive performed better in terms of yield and enantioselectivity than those with additives but the ee values remain low (Table 2, entries 7–9 vs entries 4–6). Surprisingly, in all experiments with the pre-formed catalyst 6 (Table 2, entries 4–9), a

• of alcohols as additives has a negative effect on both yield and enantioselectivity. The enantioselectivity was generally low (Table 2, entries 4–9) and with preference for the S-configured hydrocyanide employing the pre-formed Ca complex 6. In addition, product 2 was obtained with absolute

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

• −), 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

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

• , entry 3). Reducing the catalyst loading to 5 mol % slightly affected the yield of 3bb, which was 90% (Table 1, entry 4). Next, we evaluated various additives with 5 mol % of Ni(cod)2 to stabilize regenerated zero-valent nickel species (Table 1, entries 5–8). While phosphine ligands such as triphenyl

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

• the coupling with copper triflate as catalyst, without ligand, co-catalyst or other additives. The reaction involved the formation of the imine XVII followed by alkynylation to propargylamine XVIII, cyclization, and oxidation to quinoline 23 (Scheme 17) [34]. Three component oxidative annulation to

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

• , solutions of PSar homopolymer and saccharose were employed, initiating the shape transformation as well (Supporting Information File 1, Figures S33 and S35). This suggests that various hydrophilic biocompatible additives could be viable for inducing osmotic shock in shape transformation. Both PEG and PSar

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

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

• Yuki Nakanishi,
• Shoichi Sugita,
• Kentaro Okano and
• Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

• %, respectively. The highest yield of 2b was obtained in the presence of CyJohnPhos (L3) as ligand, while tricyclohexylphosphine (L2) gave the best yield in the reaction of 1c. Concerning the reaction of 1c, the use of tetra-n-butylammonium bromide and pivalic acid as additives and PCy3 (L2) as a ligand further

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• -alkyloxazolidinones, eliminating the need for any Lewis base or additives [74]. This represented a significant advancement over their previously reported work. They used six different protonated porphyrins as catalysts: TPPH4X2 (18a, X = Cl; 18b, X = Br; 18c, X = I), and TPPH4(RCOO)2 (18d, R = CF3; 18e, R = ClCH2

Advances in radical peroxidation with hydroperoxides

• Oleg V. Bityukov,
• Pavel Yu. Serdyuchenko,
• Andrey S. Kirillov,
• Gennady I. Nikishin,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

• investigated (Scheme 63b) [132]. Vicinal bis-tert-butylperoxides 204 were isolated in low yields among various oxidation products. Xu and Liu with colleagues demonstrated the influence of the solvent and additives on the chemoselectivity of iodine-catalyzed oxidation of styrenes 206 with TBHP (Scheme 64) [133

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• intermediate I. Furthermore, intermediate I subsequently undergoes another SET reaction, resulting in intermediate II and the regeneration of the photocatalyst. Intermediate II undergoes deprotonation, facilitated by the presence of Cs2CO3 as base, to yield the final products 27 or 29. Additives like BQ likely

• additives. An efficient conversion was detected when the substrate contains electron-rich functionalities. In contrast, the yield dropped notably when the amines were substituted with electron-deficient functionalities. In addition, asymmetric diaryliodonium salts were examined, and the transfer of the aryl