On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

• Daniel Straub,
• Markus Gross,
• Mona E. Arnold,
• Julia Zolg and
• Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

• mixture of right- and left-handed propellers can be resolved by chiral high pressure liquid chromatography (HPLC) into the P- and M-enantiomers, respectively [40][41]. However, due to the low racemization barrier of only about 22 kcal mol−1, the enantiomers racemize within minutes at room temperature. TTM

Data accessibility in the chemical sciences: an analysis of recent practice in organic chemistry journals

• Sally Bloodworth,
• Cerys Willoughby and
• Simon J. Coles

Beilstein J. Org. Chem. 2025, 21, 864–876, doi:10.3762/bjoc.21.70

• community risks becoming left behind without urgent cultural change. Journal data policies for the study timeframe, 01 February – 31 March 2023. ‘All data’ refers to: spectroscopic data (NMR, IR, UV–vis, Raman, circular dichroism and mass spectrometry), chromatography (GC, HPLC, SEC), physical data (m.p

Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA

• Raphael Bereiter and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56

• containing potassium and magnesium ions at a physiological pH of 7.0 for 5 hours. Analysis of the reaction mixture by anion-exchange HPLC revealed that the bromopropyl handle (C3 homolog 8) gave the highest yield of covalently tethered HBC-RNA complex (50%). Significantly less RNA alkylation yield was

• RNA aptamer, using the same conditions as described above for the first series of RNA alkylation experiments (Figure 2). Analysis by HPLC revealed that the chloropropyl HBC derivative 12 was not reactive. Surprisingly, the iodopropyl HBC derivative 13 gave significantly lower yields than its bromo

• . HPLC traces were recorded with UV absorption by 260 nm. Structure-guided approach for engineering the (non-covalent) fluorescent light-up aptamer Pepper into its covalent counterpart [11]. a) Secondary structure of the Pepper aptamer [12]; b) chemical structure of the fluorophore HBC530 [7]; c) three

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

• Maurizio Iannuzzi,
• Thomas Hohmann,
• Michael Dyrks,
• Kilian Haoues,
• Katarzyna Salamon-Krokosz and
• Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52

• )”, where A/B refers to the solvents used as mobile phase and a:b to their volume ratio. Analytical high-performance liquid chromatography (HPLC) was used to determine the purity of the obtained Fmoc-protected amino acids. The respective HPLC runs were carried out on a Primaide DAD system (VWR/Hitachi

• , Germany). The system works with a low-pressure gradient containing a HPLC pump (1110) with a 6-channel solvent degaser, an organizer, an autosampler (1210) with a 100 μL sample loop, a column oven (1310) and a diode array detector (1430). A Kinetex C18 (2) column (5 μm, 250 Å × 4.6 mm, Phenomenex

• ). After 2 h of stirring at 0 °C, H2O (30 mL) was added. After 1 h of stirring, the precipitated product was filtered, washed with H2O (15 mL), and dried in vacuo at 60 °C to give 6 (7.81 g, 9.39 mmol, 95%, 91% purity determined by analytical HPLC) as an orange solid. The crude was used without further

Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

• Rémy B. Teponno,
• Sara R. Noumeur and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

• each as white powder after HPLC purification of the mixture formed from reaction of massarilactone D with cinnamoyl chloride in triethylamine in the presence of catalytic amounts of 4-dimethylaminopyridine. The ESIMS of compound 3 exhibited the sodium adducts at m/z 507.20 [M + Na]+ and 991.39 [2M + Na

• Anton Paar MCP-150 Polarimeter with sodium D line at 589 nm and 100 mm path length. HRESIMS mass spectra were measured with a maXis ESI TOF mass spectrometer (Bruker Daltonics) [scan range m/z 100–2500, rate 2 Hz, capillary voltage 4500 V, dry temperature 200 °C], coupled to an Agilent 1200 series HPLC

• hertz (Hz). HPLC-DAD-MS analysis was performed using an amaZon speed ETD ion trap mass spectrometer (Bruker Daltonics) in positive and negative ionization modes. The mass spectrometer was coupled to a DIONEX UltiMate 3000 diode array detector [column 2.1 × 50 mm, 1.7 μm, C18 Acquity UPLC BEH (Waters

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

• Wei-Jin Chang,
• Sook Yee Liew,
• Thomas Kurz and
• Siow-Ping Tan

Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46

• ,f) often precipitated out of the reaction mixture and were sufficiently pure (>95% by HPLC) after the simple washing steps, and the more polar hydantoin products could be extracted out of the reaction mixture with ethyl acetate and did not require further chromatographic purification. The “one-pot

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• : Experimental procedures, characterization data, NMR spectra, and HPLC chromatograms. Funding This research was funded by an IAAR Research Support Program (Chiba Halogen Science: Halogen-Linkage of Molecular Functions); Chiba University Open Recruitment for International Exchange Program, Chiba University

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

• a relatively fast and efficient conversion into the desired products. Further optimization of this promising photochemical method is currently under way in our laboratory. Isolation and characterization Pure samples of 9,10-ANTH(BnF)2 and 9-ANTH(BnF) were isolated by HPLC (Figure S3, Supporting

• photoirradiated 9,10-ANTH(BnF)2 solution contained only resonances for the starting material (20%) and for a single presumed photoproduct (80%) which retained the symmetry of 9,10-ANTH(BnF)2 (see Supporting Information File 1, Figures S7 and S9 (19F NMR)). An HPLC analysis of the photoirradiated ANTH solution

• revealed that at least three compounds were present, in accordance with an earlier report [32]. In the photoirradiated 9,10-ANTH(BnF)2 sample, the HPLC chromatogram shown in Figure S10 (Supporting Information File 1) showed 9,10-ANTH(BnF)2 (tR = 4.5 minutes) and a major product (tR = 6 minutes), in

Synthesis of the aggregation pheromone of Tribolium castaneum

• Biyu An,
• Xueyang Wang,
• Ao Jiao,
• Qinghua Bian and
• Jiangchun Zhong

Beilstein J. Org. Chem. 2025, 21, 510–514, doi:10.3762/bjoc.21.38

• , Mori and Phillips achieved the complete separation of the derivatives from the four stereoisomers by reversed-phase HPLC at −54 °C, and revealed that the natural pheromone consists of four stereoisomers of 4,8-dimethyldecanal (Figure 1) [16][17]. Previous syntheses mainly focused on chiral sources of

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

• (16) see Supporting Information File 1. Syntheses of haloalkyl- and mesyloxyalkyl-modified preQ1 as and DPQ1 ligands. Supporting Information Supporting Information File 12: Experimental part, HPLC analysis of preQ1 and NMR spectra. Acknowledgements We thank Clemens Eichler (University of Innsbruck

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

• its enantioselectivity, aliquots of the reaction mixture were taken at defined time intervals and analyzed by HPLC using a chiral column after passing them through a short silica gel pad. Some interesting conclusions can be made from the data in Table 1. Firstly, the retro-Michael reaction occurs, to

• –240 mesh). Chiral HPLC analysis was performed using different chiral columns. IR spectra were recorded on an FTIR instrument. High-resolution mass spectra were performed by positive electrospray ionization using a quadrupole-time-of-flight detector (ESI+-Q-TOF) instrument. All compounds were purchased

• resolution of pure diastereomer anti-1. Supporting Information Supporting Information File 10: Characterization data, copies of spectra and HPLC chromatograms. Funding J.G.-P. thanks to the Universidad de Valladolid for a predoctoral fellowship. The Spanish MINECO (Project CTQ2014-59870 P) and the Junta de

Identification and removal of a cryptic impurity in pomalidomide-PEG based PROTAC

• Bingnan Wang,
• Yong Lu and
• Chuo Chen

Beilstein J. Org. Chem. 2025, 21, 407–411, doi:10.3762/bjoc.21.28

• impurity generated in this process. Nucleophilic acyl substitution competes with aromatic substitution to displace glutarimide and gives a byproduct that can co-elute with the desired product on HPLC throughout the remainder of the synthesis. Scavenging with taurine is a convenient way to minimize this

• iVeliparib-AP6. As a common practice for small-molecule library synthesis, the identity and the purity of the reaction products of this simple, 3-step process were analyzed by LC–MS. Whereas the HPLC traces of the reaction mixtures showed one major product peak, the final product carried a barely noticeable

• shoulder peak (Figure 2, marked with asterisk). A close examination of the UV profile indicated the presence of an impurity. Its removal requires repetitive prep-HPLC purifications that are inefficient and time-consuming. The isolated impurity lacks the characteristic fluorescent yellow color of

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

• were obtained using a J-815 spectropolarimeter (JASCO Pfungstadt, Germany). The optical rotation, ECD, and UV–vis spectra of the newly described secondary metabolites were assessed in MeOH (Uvasol, Merck, Darmstadt, Germany). Analytical HPLC chromatograms and electrospray ionization mass spectra (ESIMS

• range from 190 to 600 nm. High-resolution electrospray ionization mass spectra (HRESIMS) were obtained using an Agilent 1200 Infinity Series HPLC-UV system (Agilent Technologies, Santa Clara, CA, USA) equipped with a C18 Acquity UPLC BEH analytical column (50 × 2.1 mm, 1.7 µm; Waters, Milford, MA, USA

• acetone/MeOH (9:1, 7:3, 1:1, 0:1) along with one last fraction of MeOH 100% using 0.1% formic acid. Nine fractions of 1 L each were eluted that were collected and evaporated separately under reduced pressure to dryness. For fractions 3, 4, 6 and 8 were further purified using a PLC 2250 preparative HPLC

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

• +) couple. Electrolyte solutions, at a concentration 0.1 M, were prepared from anhydrous, degassed HPLC grade CH2Cl2 and anhydrous Bu4NPF6. Voltammograms were recorded at a sweep rate of 100 mV s−1. Sample concentrations were ca. 1–2 mM. Electronic spectroscopy UV–vis–NIR spectroelectrochemical studies were

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

• reaction mixture was neutralized by HCl aqueous solution, extracted with ether, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane and ethyl acetate 8:2 and recycling HPLC using chloroform as the

• concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane and ethyl acetate 8:2 and recycling HPLC using chloroform as the eluent to give 0.68 g of I1 in 56% yield. 1H NMR (300 MHz, CDCl3, TMS) δ = 2.09 (s, 3H, CH3), 2.46 (s, 3H, CH3), 7.27 (s, 1H, aromatic H

• HPLC using chloroform as the eluent to give 0.39 g of I2 in 41% yield. 1H NMR (300 MHz, CDCl3, TMS) δ = 2.31 (s, 3H, CH3), 2.47 (s, 3H, CH3), 7.47–7.51 (m, 3H, aromatic H), 7.72 (q, 1H, aromatic H), 7.98–8.01 (m, 2H, aromatic H); 13C NMR (75 MHz, CDCl3) δ = 12.1, 16.4, 114.8, 126.9, 129.3, 131.2, 132.8

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

• MassLynx ver. 4.1 and data analysis was done using Waters OpenLynx browser ver. 4.1. Solvents were commercial HPLC grade and used without further purification. The substrates 2a, 7a, and 8a were commercially available and used without further purification. The substituted β-nitrostyrenes 1a and 3a–6a were

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

• consists of a fluid delivery system, mixing tools, reactors, quenching units, pressure regulation units, and collection vessels. The fluid delivery is normally executed using either high-pressure liquid chromatography (HPLC), a syringe, or peristaltic pumps. A passive mixing stage where the reagents are

• drug molecules autonomously, and it does not include a closed-loop optimization framework. The Pfizer research team developed a custom-designed flow system for rapid reaction screening of the Suzuki–Miyaura coupling reaction on a nanomolar scale [50]. The platform included a modified HPLC system that

• reaction, employing a "black-box" optimization strategy directed by Nelder–Mead simplex method algorithm [57]. In-line HPLC analysis was performed to determine the product yield in real time and give feedback to the control system to direct the input conditions to achieve the optimum product yield in 19

Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• ), as well as additional signals not matching those of any known psammaplysin derivatives. Further separation of this fraction using C18 HPLC led to the isolation of ceratinadin G (1, 0.4 mg, 3.2 × 10−4%) along with psammaplysin F (2) [10][11][12]. Ceratinadin G (1) was isolated as an optically active

• [silica gel 60N (spherical, neutral, 40–50 µm), Kanto Chemical Co., Inc.; 38 × 350 mm; eluent CHCl3/MeOH 100:0 to 0:100], yielding 18 fractions (Fr. 1–18). A portion (17.0 mg) of the fraction Fr. 14 (32.5 mg) was further separated by C18 HPLC (COSMOSIL 5C18-AR-II, 10 × 250 mm, Nacalai tesque Inc.; eluent

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• HPLC (RP-HPLC), which led to the purification of the known metabolites, ianthelliformisamines A–C (1–3) [7] and aplysterol (8) [13], and four new natural products, ianthelliformisamines D–G (4–7) (Figure 1). This extraction and isolation process was repeated twice to obtain sufficient quantities of the

• ETD ESI-qTOF. Alltech Davisil (30–40 µm, 60 Å) C8-bonded silica and Alltech Davisil (30–40 µm, 60 Å) diol-bonded silica were used for pre-adsorption work before RP- or NP-HPLC, respectively. The pre-adsorbed material was subsequently packed into an Alltech stainless steel guard cartridge (10 × 30 mm

• ) then attached to a HPLC column prior to fractionation. A Waters 600 pump fitted with a Waters 996 photodiode array detector fitted with a Gilson 717-plus autosampler were used for RP-HPLC separations. A Thermo Fisher Scientific Dionex Ultimate 3000 UHPLC was used for NP-HPLC separations. Thermo Betasil

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

• Lucía Campos-Prieto,
• Aitor García-Rey,
• Eddy Sotelo and
• Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

• compounds with high yields (84–92%). The three most promising compounds of the library (13a, 13b, and 13c) were selected for further detailed characterization. In vitro evaluation was performed employing a high-performance liquid chromatography (HPLC)-based methodology, using the fluorogenic histone

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

• hypothesis that the reaction would work in acidic environment using catalysts insensitive to pH-induced aggregation. In the same aldol reaction, using of macrocycles 60 and 61 containing chiral secondary amine moieties provided not only good yields, but also good diastereoselectivities; chiral HPLC analysis

Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide

• Noble Brako,
• Sreerag Moorkkannur Narayanan,
• Amber Burns,
• Layla Auter,
• Valentino Cesiliano,
• Rajeev Prabhakar and
• Norito Takenaka

Beilstein J. Org. Chem. 2024, 20, 3069–3076, doi:10.3762/bjoc.20.255

• enantiomeric ratios were determined by HPLC on a chiral stationary phase. Evaluation of the extent to which (S)-8 catalyzed the allenylation reaction. Reaction conditions: aldehyde 1a–k (0.1 mmol), silane (0.15 mmol), (S)-8 (0.01 mmol), CH2Cl2 (0.4 mL). Enantiomeric ratios were determined by HPLC on a chiral

• Information File 10: Experimental details, characterization data, spectra, and HPLC traces. Acknowledgements We thank the Florida Institute of Technology and University of Miami for the generous support of the instrumentation facility. Funding This work was financially supported by a grant from the National

Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins

• Mike Brockmann,
• Jonas Lobbel,
• Lara Unterriker and
• Rainer Herges

Beilstein J. Org. Chem. 2024, 20, 2954–2958, doi:10.3762/bjoc.20.248

• -substituted Ni porphyrins 29 (78%), 30 (97%), and 31 (57%). The latter were treated with LiOH and HCl to give the free acids 32 (94%), 33 (39%), and 34 (45%). The HPLC–ESIMS analysis of 32, 33, and 34 revealed that two major atropisomers of each porphyrin had formed. In 32 both atropisomers exhibit a roughly

• Information File 42: Experimental procedures, characterization data of all products, and copies of 1H, 13C, and 19F NMR spectra. Acknowledgements We thank Dr. Claus Bier for the help with the HPLC–ESIMS measurements.

4,6-Diaryl-5,5-difluoro-1,3-dioxanes as chiral dopants for liquid crystal compositions

• Maurice Médebielle,
• Peer Kirsch,
• Jérémy Merad,
• Carolina von Essen,
• Clemens Kühn and
• Andreas Ruhl

Beilstein J. Org. Chem. 2024, 20, 2940–2945, doi:10.3762/bjoc.20.246

• purification. Ketalization of rac-2 with liquid crystal-like ketone 1 [43] (in toluene) or 2,2-dimethoxypropane 5 (in THF) provided dioxanes rac-3 and rac-4 in 56% and 62% yields, respectively (Scheme 2). Samples of rac-3 and rac-4 were separated by preparative HPLC on a chiral phase. Suitable crystals of all

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

• chemistry on the histone H2A protein. The protein was demonstrated as the T120C mutant via site-directed mutagenesis in Escherichia coli and decontaminated by HPLC. A notable reconciliation was changing the aqueous buffer from HEPES to phosphate owing to side-product generation during the arylation in HEPES

• . The reaction of H2A with the diaryliodonium salt in phosphate buffer resulted in the expected arylated conjugate in an hour with a maximum of 98% conversion, yielding sulfur arylated product in 54% isolated yield after purification by HPLC. Additionally, the functionalization of the ketone with a

• high conversions (83–93%) in 1–20 hours. Purification by HPLC yielded the isolated oxime conjugates in excellent amounts. This methodology presents a promising approach for the late-stage variation of proteins and peptides, offering versatility and efficiency in aqueous environments. In addition to