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

• BPP 2 and BPP-OiPr 3. Supporting Information Supporting Information File 114: Experimental and computational details, X-ray crystallography, synthesis and characterization of new compounds, additional PL, mass, and NMR spectra, and theoretical calculations. Acknowledgements We appreciate the help

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

• Dmitry E. Shybanov,
• Maxim E. Kukushkin,
• Eugene V. Babaev,
• Nikolai V. Zyk and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

• alcohol 2. Its 1H NMR spectrum contained a triplet with a coupling constant of 5.1 Hz at 5.52 ppm and a doublet at 4.30 ppm. In methanol, ethanol and petroleum ether, with an increasing reaction time, a significant amount of product 3 was observed in the 1H NMR spectra of the mixtures, as identified by

• was confirmed through the three-component reaction with acetylacetone, in which only the product 7 was formed (according to 1H NMR spectra of the reaction mixture). Stereoselective interactions between methylidene adducts and cyclopentadiene were confirmed for three-component reactions involving

• was also studied using isoprene as an example. In reactions involving Meldrum's acid, the formation of an inseparable mixture of the two stereoisomeric products 14a and 14b in a ratio of 95:5 was detected with a yield of 91%, the 1H NMR spectra of which coincided with those described in the literature

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

• , and copies of NMR spectra. Funding This work was supported by the Talent Project of Fuyang Normal University (No. XJRCXM202232), the College Students Innovative Entrepreneurial Training Plan Program (No. S02310371028), The Natural Science Foundation of Higher Education Institutions in Anhui Province

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

• previous work [56][57], whereas compounds N4 and I1–I4 were synthesized according to Scheme 2 in the Experimental section. The chemical structures of all compounds were confirmed by 1H NMR and 13C NMR spectroscopy and high-resolution mass spectrometry. 1H NMR and 13C NMR spectra are shown in Supporting

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

• . Optimization of reaction conditions.a Supporting Information Supporting Information File 102: Experimental procedures, product characterization, and copies of NMR spectra. Funding We are grateful to the Scientific Research Project of Hubei Education Department (T2020023 and Q20211402) and the open project of

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

• Asahi Kanno,
• Ryo Tanifuji,
• Satoshi Yoshida,
• Sota Sato,
• Saori Maki-Yonekura,
• Kiyofumi Takaba,
• Jungmin Kang,
• Kensuke Tono,
• Koji Yonekura and
• Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

• by small crystal analysis using an X-ray free-electron laser (XFEL) [54][55]. aSee Supporting Information File 1 for details. Supporting Information Supporting Information File 100: The experimental procedures and characterization data, including copies of NMR spectra and X-ray crystallographic

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

• methods, synthetic procedures, analytical data and exemplary copies of NMR spectra of novel compounds. Supporting Information File 97: CheckCIF report for 7b. Supporting Information File 98: CIF file for 7b. Acknowledgements We acknowledge the mass spectrometry facility of the University of Crete

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

• species, the counteranion is BF4−. C) Possible interactions that interfere with the titration outcomes. A) HB complex formation between a donor and tri-n-butylphosphine oxide. B) 1H NMR spectra of 2b (5.0 mM) in the presence of different concentrations of tri-n-butylphosphine oxide in anhydrous CD3CN at

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

• 2444.3405, respectively. Stacked 1H NMR spectra (CDCl3/CD3CN 1:1, v/v, 400 MHz, 298 K) of G1 upon addition of different equiv of H1 ([G1] = 1.0⋅10−3 M). (a) 0.0 equiv, (b) 0.2 equiv, (c) 0.4 equiv, (d) 0.6 equiv, (e) 0.8 equiv, (f) 1.0 equiv, (g) 1.2 equiv, (h) 1.4 equiv, and (i) only H1. Single-crystal X

• the π–π-stacking distances (d[π···π] = 3.3–3.4 Å) between H2 and G1. The side chains of H2 were replaced by a methyl group, all hydrogen atoms except amide groups, solvent molecules, and counterions were omitted for clarity. Stacked 1H NMR spectra (CDCl3/CD3CN 1:1, v/v, 400 MHz, 298 K) of G2 upon

• ). Stacked 1H NMR spectra (CDCl3/CD3CN 1:1, v/v, 400 MHz, 298 K) of G2 and Zn2+ upon addition of different equiv of H1 ([G2 + Zn2+] = 1.0⋅10−3 M). (a) 0.0 equiv, (b) 0.4 equiv, (c) 0.6 equiv, (d) 0.8 equiv, (e) 1.0 equiv, (f) 1.2 equiv, (g) 1.4 equiv, and (h) only H1. Specific viscosity of the linear

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

• aromatic compounds. Experimental NMR spectra were recorded on Bruker Avance 400 MHz or Bruker Avance III HD 600 MHz spectrometers. Residual solvent peaks (CDCl3, D2O, CD3OD, (CD3)2SO) were used as internal standard (7.26, 4.79, 3.31, and 2.50 ppm for 1H, and 77.16, 49, and 39.52 ppm for 13C, respectively

• (entries 1–6). The isolated product yields were obtained by performing the reactions at 80 °C for the time indicated beside each product. For more details, see the experimental section below. Supporting Information Supporting Information File 68: 1H and 13C NMR spectra of the synthesized compounds, the

Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

• Yongming Xiong,
• Xue Lin Ma,
• Shilong Su and
• Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

• . This corresponds to a molecular formula of C119H122O9, which is in agreement with the fully fused product 11 in its protonated form. Unfortunately, clean 1H and 13C NMR spectra of this product could not be obtained to allow full characterization of this product. Efforts to increase the yield of 11

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• , characterization data, and copies of 1H and 13C{1H} NMR spectra. Acknowledgements The data presented in this article are partially taken from the M.Sc. theses of Merve Yence (Bilkent University, 2019) and Dilgam Ahmadli (Bilkent University, 2021). Funding Financial support for some parts of this work from the

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• the electrophilic amination of tert-butyl 3-(p-tolylsulfinyl)propanoate (4a) with BBX 2a (0.23 mmol of limitant in 2 mL of solvent). Supporting Information Supporting Information File 54: Experimental procedures, characterization data, NMR spectra, and X-ray diffraction data. Funding The authors

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

• positions. The similarity of the 19F NMR spectra of F and alkoxy-substituted derivatives, Fn, showing 6 single peaks, corresponding to the 8 different fluorine atoms at almost identical positions (Figures S8–S14 and S21 in Supporting Information File 1), confirms that the pattern of the annulation reaction

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

• . Supporting Information File 48: Additional experimental details and copies of 1H and 13C{1H} NMR spectra. Acknowledgements We thank Professor Shigeki Mori and Ms. Rimi Konishi (Ehime University) for the X-ray crystallographic analysis.

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

• -1500 spectropolarimeter. 1H and 13C NMR spectra were acquired on a Bruker Avance II 600 MHz NMR spectrometer equipped with a cryoplatform, using 3.0 mm micro cells (Shigemi Co., Ltd.) for CD3OD. The 1H NMR chemical shift of residual CD2HOD in CD3OD at 3.35 ppm and the 13C NMR chemical shift of CD3OD at

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

• biological profiling. Experimental General experimental procedures Specific rotations were recorded using a JASCO P-1020 polarimeter. UV data was recorded on a JASCO V-650 UV–vis spectrophotometer. NMR spectra were recorded at 25 °C on a Bruker Avance III HD 800 MHz NMR spectrometer equipped with a cryoprobe

• ) were collected and resulted in the purification of synthetic Ianthelliformisamine D (4, 11.1 mg, tR 21 min, 16% yield). The 1H and 13C NMR spectra of the synthetic compound matched that of the natural product. Synthetic Ianthelliformisamine D (4): Clear film: 1H NMR (DMSO-d6, 800 MHz) δH 8.04 (t, J

• ). NMR data of ianthelliformisamines D (4) and E (5) in DMSO-d6.a NMR data of ianthelliformisamines F (6) and G (7) in DMSO-d6.a Supporting Information Supporting Information File 44: NMR data tables for compounds 4–7, 1D and 2D NMR spectra of compounds 4–7, 1H NMR spectra of natural products 1–3 and 8

Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling

• John M. Halford-McGuff,
• Thomas M. Richardson,
• Aidan P. McKay,
• Frederik Peschke,
• Glenn A. Burley and
• Allan J. B. Watson

Beilstein J. Org. Chem. 2024, 20, 3198–3204, doi:10.3762/bjoc.20.265

• /53959471-068e-483e-bcd4-920e6761926b and CCDC 2355570 contains the supplementary crystallographic data for this study. Supporting Information File 38: Characterization data and copies of NMR spectra. Supporting Information File 39: Crystallographic information file (cif) for compound 13. Supporting

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

• Radell Echemendía,
• Carlee A. Montgomery,
• Fabio Cuzzucoli,
• Antonio C. B. Burtoloso and
• Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

• Information File 32: Experimental part, NMR spectra, computational details and crystallgraphic data. Acknowledgements We would like to acknowledge the Schipper lab at the University of Waterloo for providing access to the microwave reactor used in this study. We would also like to acknowledge Boris Ragula

Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

• Thierry Milcent,
• Pascal Retailleau,
• Benoit Crousse and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

• analysis (Figure 5). Consequently, it was possible to assess the stereochemistry of the other diastereoisomer 8f’ and their precursors 7f and 7f’. On the other hand, considering the similarities of the 1H NMR spectra of the CF2H and CF3 analogs, by comparison, we could hypothesize the absolute

• phenylalanine) indicate that they are not involved in hydrogen bonds. Furthermore, the 2D 1H-1H NOE NMR spectra and the chemical shifts of the NH protons of compounds 8f’, 8e, and 8e’ did not show any significant differences compared to 8f. Overall, the ability of the new fluorinated β-analogs of

• Supporting Information File 30: Experimental procedures, product characterization, X-ray analysis and copies of NMR spectra. Acknowledgements The authors gratefully acknowledge Central Glass Co. for the gift of trifluoro- and difluoroacetaldehyde hemiacetal.

Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF₅- and CF₃SF₄-containing [2]staffanes

• Jón Atiba Buldt,
• Wang-Yeuk Kong,
• Yannick Kraemer,
• Masiel M. Belsuzarri,
• Ansh Hiten Patel,
• James C. Fettinger,
• Dean J. Tantillo and
• Cody Ross Pitts

Beilstein J. Org. Chem. 2024, 20, 3134–3143, doi:10.3762/bjoc.20.259

• procedures, characterization data, NMR spectra, computational details, and X-ray crystallographic experimental details. Supporting Information File 16: LTP X-ray crystal structure of compound 3 (2357079.cif), HTP X-ray crystal structure of compound 3 (2357080.cif) and X-ray crystal structure of compound 2 at

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• Information File 12: Experimental procedures, compound characterization data, and copies of NMR spectra. Funding C.M. A-M. (756225) and América A. Frías-López (833463) acknowledges the support of CONACHYT through a graduate scholarship. This work was financially supported by Instituto De Ciencia, Tecnología

Extension of the π-system of monoaryl-substituted norbornadienes with acetylene bridges: influence on the photochemical conversion and storage of light energy

• Robin Schulte,
• Dustin Schade,
• Thomas Paululat,
• Till J. B. Zähringer,
• Christoph Kerzig and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 3061–3068, doi:10.3762/bjoc.20.254

• section and complete set of NMR spectra. Funding Financial support was provided by the University of Siegen. R.S. is grateful to the House of Young Talents (University of Siegen) and the Stiftung Nagelschneider for the Ph.D. fellowships. T.J.B.Z. thanks the Deutsche Bundesstiftung Umwelt (DBU) for a Ph.D

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• and compound characterization data, solvatochromic studies for compound 1с, titration data, and 1H and 13C NMR spectra for compounds 1a–i. Funding This work was performed within the framework of the state task of the Ministry of Science and Higher Education of the Russian Federation (project no. FEGR

Tailored charge-neutral self-assembled L₂Zn₂ container for taming oxalate

• David Ocklenburg and
• David Van Craen

Beilstein J. Org. Chem. 2024, 20, 3007–3015, doi:10.3762/bjoc.20.250

• sufficient quality to obtain a solid-state structure of the oxalate host–guest complex [(C2)@L2Zn2]2− so that we utilized DFT calculations to model the expected structure of the host–guest species (Figure 3a). Therefore, we funneled structural information obtained from NMR spectra into our starting geometry

• Information Supporting Information File 2: Synthetic protocols, characterization data, NMR spectra, guest binding investigations, data fitting, and computational modeling details. Funding The authors are grateful for financial support by the Fonds der Chemischen Industrie (FCI) through a Liebig grant and the