Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air

• Yuki Yamamoto,
• Yuki Konakazawa,
• Kohsuke Fujiwara and
• Akiya Ogawa

Beilstein J. Org. Chem. 2024, 20, 2577–2584, doi:10.3762/bjoc.20.216

• characterization data are provided in Supporting Information File 1. Comparison of the crude mixture of the reactions under (a) argon atmosphere or (b) open-air. (a) Conventional methods for the generation of Ar• from Ar3Bi, (b) our previous studies, and (c) this work. Scope for transition-metal-free synthesis of

• File 138: Investigation of the boron residue in the crude mixture by 11B NMR measurement, characterization data of the compounds, and copies of 1H NMR and 13C{1H} NMR spectra. Acknowledgements We acknowledged Dr. Tran Dat Phuc and Mr. Soichiro Mita (Osaka Prefecture University) for their initial

Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures

• Yohei Haketa,
• Takuma Matsuda and
• Hiromitsu Maeda

Beilstein J. Org. Chem. 2024, 20, 2567–2576, doi:10.3762/bjoc.20.215

• further purification unless otherwise stated. According to the previous procedure [30], 4,8,12-tris(2,6-dimethylphenyl)-4,8,12-triazatriangulenium as a Cl− ion pair, 2+-Cl−, was prepared. NMR spectra used in the characterization of products were recorded on a JEOL ECA-600 600 MHz spectrometer. All NMR

HFIP as a versatile solvent in resorcin[n]arene synthesis

• Hormoz Khosravi,
• Valeria Stevens and
• Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

• showed resorcinol in the reaction mixture. This observation led us to run a control experiment in the absence of aldehyde, which showed that HFIP leads to metal-free deiodination of 2-iodoresorcinol (Figure 1a). Finally, while all new compounds reported herein have full spectroscopic characterization

Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams

• Valentina Giraldi,
• Giandomenico Magagnano,
• Daria Giacomini,
• Pier Giorgio Cozzi and
• Andrea Gualandi

Beilstein J. Org. Chem. 2024, 20, 2461–2468, doi:10.3762/bjoc.20.210

• characterization, spectroscopic data for new compounds, and copies of NMR spectra. Funding P. G. C., D. G., and A. G. acknowledge the University of Bologna for financial support. MIUR national project (PRIN 2017 ID: 20174SYJAF) SURSUMCAT “Raising up Catalysis for Innovative Developments” and European Union’s

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

• Smaher E. Butt,
• Konrad Kepski,
• Jean-Marc Sotiropoulos and
• Wesley J. Moran

Beilstein J. Org. Chem. 2024, 20, 2455–2460, doi:10.3762/bjoc.20.209

• Information File 120: Experimental procedures, compound characterization data, copies of NMR spectra, cartesian coordinates and energies of calculated structures. Acknowledgements We thank Professor Mark Heron for his useful discussions and Dr Neil McLay for his NMR expertise. We also acknowledge Joshua

Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt

• Dominik L. Reinhard,
• Anna Schmidt,
• Marc Sons,
• Julian Wolf,
• Elric Engelage and
• Stefan M. Huber

Beilstein J. Org. Chem. 2024, 20, 2401–2407, doi:10.3762/bjoc.20.204

• TOFs of the strongest activators 2BArF, 7BArF, and 4BArF (and their calculated standard deviation). The TOFs were determined from the kinetics (see Supporting Information File 1 for further details). Supporting Information Supporting Information File 107: Synthesis, catalyses, and characterization

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• ), ABTS•+ and CUPRAC assays expressed as IC50 and TEAC. Supporting Information Supporting Information File 100: Experimental procedures and characterization data. Funding This work was supported by the Russian Science Foundation, grant 23-13-00201.

Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

• Yuri A. Sidunets,
• Valeriya G. Melekhina and
• Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

• . Supporting Information Supporting Information File 96: Experimental procedures, characterization data of all products, copies of 1H, 13C NMR, 15N spectra of new compounds, DSC curves,X-ray crystallographic data and copies of IR spectra. Acknowledgements The crystal structure determination was performed at

Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

• Andreas Wiest and
• Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

• disease [2][3]. In parallel, mass spectrometry (MS) has been crucial in many areas centered around the characterization of NPs [4]. First to annotate their often complex structures using diverse fragmentation techniques [4]. Nowadays, MS is applied for the identification of NPs’ cellular protein targets

• and amino acid remain unknown. In contrast, the peptide-level identification is focused on the characterization of the actual probe-modified peptides. It might be more challenging as a larger protein amount to start with is necessary and the fragments of the probe-modified peptides may not be trivial

• unmodified protein. MS-based chemical proteomics without enrichment The aim of this approach is to isolate and characterize the probe–peptide conjugate and hence to provide direct evidence of the probe–protein interaction [80]. In principle, the direct characterization of the probe–peptide conjugate can be

Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

• Phong Thai,
• Lauv Patel,
• Diyasha Manna and
• David C. Powers

Beilstein J. Org. Chem. 2024, 20, 2305–2312, doi:10.3762/bjoc.20.197

• NMR using triethyl 1,3,5-benzenetricarboxylate as internal standard. Supporting Information Supporting Information File 92: Experimental procedures and characterization data, original spectra of new compounds, and optimization details. Funding The authors acknowledge the Welch Foundation (A-1907

gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu₄NBF₄ or electrogenerated acid

• Mizuki Yamaguchi,
• Hiroki Shimao,
• Kengo Hamasaki,
• Keiji Nishiwaki,
• Shigenori Kashimura and
• Kouichi Matsumoto

Beilstein J. Org. Chem. 2024, 20, 2261–2269, doi:10.3762/bjoc.20.194

• for 2a. Plausible reaction mechanism. Optimization of the gem-difluorination of hex-5-yn-1-ylbenzene (1a) to form difluorinated compound 2a (method A). Scope and limitations. Supporting Information Supporting Information File 84: Experimental procedure, characterization data of compounds and copies

Synthesis and reactivity of the di(9-anthryl)methyl radical

• Tomohiko Nishiuchi,
• Kazuma Takahashi,
• Yuta Makihara and
• Takashi Kubo

Beilstein J. Org. Chem. 2024, 20, 2254–2260, doi:10.3762/bjoc.20.193

• spectrum shape (Supporting Information File 1, Figure S10). On the other hand, the UV–vis spectrum of the DAntM cation, generated from 3 in TFA solution, showed an intense absorption band at 890 nm, which is the opposite trend compared to the DAntM radical. Conclusion The synthesis and characterization of

• . Decomposition pathway of the DAntM radical under air conditions. Supporting Information Supporting Information File 81: Synthetic procedure and compound characterization data (1H, 13C NMR, MS, melting point, X-ray crystallography) of new compounds. DFT calculation results and optimized structural Cartesian

Electrochemical allylations in a deep eutectic solvent

• Sophia Taylor and
• Scott T. Handy

Beilstein J. Org. Chem. 2024, 20, 2217–2224, doi:10.3762/bjoc.20.189

• using a scoopula for further use and analysis using a Thermo Scientific Niton XL3t X-Ray Fluorescent Spectroscopy analyzer. Product characterization 1-(4-Methoxyphenyl)-3-buten-1-ol [39]: 1H NMR (300 MHz, CDCl3) 7.27 (d, J = 8.58, 2H), 6.86 (d, J = 5.82, 2H), 5.83–5.73 (m, 1H), 5.17–5.10 (m, 2H), 4.67

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

• Andrey R. Galeev,
• Maksim V. Dmitriev,
• Alexander S. Novikov and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2024, 20, 2208–2216, doi:10.3762/bjoc.20.188

• ), 2356154 (3bb) and 2356153 (3ca) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via https://www.ccdc.cam.ac.uk/structures. Supporting Information File 63: Full experimental details, characterization

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• . Characterization of all the compounds were accomplished using 1H, 13C NMR, and HRMS. See Supporting Information File 1 for the respective spectra. The “*’’ wherever present in NMRs spectra denotes solvent residual peaks. Chemical shifts are recorded in units of δ (ppm), and referenced with respect to the standard

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• 52: Experimental procedures and characterization data of new compounds. Acknowledgements The authors are grateful to Enamine Ltd. (Kyiv, Ukraine) for NMR/HRMS support. The authors also thank Charite University of Medicine, Germany (Institute for Physiology, Structural Bioinformatics Group), Federal

From perfluoroalkyl aryl sulfoxides to ortho thioethers

• Yang Li,
• Guillaume Dagousset,
• Emmanuel Magnier and
• Bruce Pégot

Beilstein J. Org. Chem. 2024, 20, 2108–2113, doi:10.3762/bjoc.20.181

• . The scope of aryl perfluoromethyl sulfoxides and a selenoxide. The scope of alkyl nitriles. Optimization of the reaction conditions. Supporting Information Supporting Information File 48: Experimental procedures, characterization data of all isolated products as well as copies of NMR spectra for

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates

• Deepa Nair,
• Abhishek Tiwari,
• Banamali Laha and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2024, 20, 2016–2023, doi:10.3762/bjoc.20.177

• . Reaction optimisation using phase-transfer catalysts.a Scope of alkylidenemalonates and curcumins.a Supporting Information Supporting Information File 38: Experimental procedures and characterization data. Supporting Information File 39: Copies of NMR spectra of all new compounds. Supporting Information

Development of a flow photochemical process for a π-Lewis acidic metal-catalyzed cyclization/radical addition sequence: in situ-generated 2-benzopyrylium as photoredox catalyst and reactive intermediate

• Masahiro Terada,
• Zen Iwasaki,
• Ryohei Yazaki,
• Shigenobu Umemiya and
• Jun Kikuchi

Beilstein J. Org. Chem. 2024, 20, 1973–1980, doi:10.3762/bjoc.20.173

• , experimental procedures, and characterization data. Supporting Information File 30: Copies of NMR spectra. Funding This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand” (JP17H06447) and a Grant-in-Aid for

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

• Siham Asyiqin Shafie,
• Ryo Nozawa,
• Hideaki Takano and
• Hiroshi Shinokubo

Beilstein J. Org. Chem. 2024, 20, 1967–1972, doi:10.3762/bjoc.20.172

• . Supporting Information Supporting Information File 26: Experimental procedures, compound characterization data including NMR and MS spectra, additional crystal data and details from DFT calculations. Funding This work was supported by Japan Society for the Promotion of Science (JSPS) KAKENHI grants

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• : Characterization of all compounds (1H NMR, 13C NMR, LC–MS, IR), and crystallographic methods and data for products P1 and P2. Supporting Information File 23: DFT methods, relative energy comparisons, TS imaginary frequencies, and XYZ coordinates. Supporting Information File 24: GoodVibes outputs. Acknowledgements

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

• Ze-Nan Hu,
• Yan-Hui Wang,
• Jia-Bing Wu,
• Ze Chen,
• Dou Hong and
• Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

• characterization data, and spectra. Funding This work was financially supported by the National Natural Science Foundation of China (numbers 22071116 and 21772096).

Novel oxidative routes to N-arylpyridoindazolium salts

• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

• reported as substrates for nucleophilic substitutions using potassium fluoride [22]. The study is in progress now. Voltammetry characterization of the N-arylpyridoindazolium salts S1–S3 and their precursors, diarylamines A1–A3 The electrochemical investigation of the new salts was performed at a Pt

Electrochemical radical cation aza-Wacker cyclizations

• Sota Adachi and
• Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

• cyclization.a Supporting Information Supporting Information File 6: General remarks and characterization data, including copies of 1H and 13C NMR spectra. Funding This work was supported in part by JSPS KAKENHI Grant No. 22K05450 (to Y. O.), and TEPCO Memorial Foundation (to Y. O.).

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• antibiotics against drug-resistant pathogens. Although certain RiPPs with activity against Clostridia have been described [31], the characterization of complete gene clusters encoding for lantibiotics, using their native biosynthetic machinery and not that of nisin or of other non-native peptides, as well as

• the chemical characterization of the NPs that are produced and the modifications they suffer, from a Clostridium genus, have yet to be accomplished. This is due to the difficulty in isolating and maintaining such strains in the laboratory and the limited availability of genome sequences compared to

• chemical structures of these lantibiotics make them promising candidates for treating drug-resistant pathogens, and the characterization of these compounds from Clostridium provides an opportunity to develop new antibiotics. Results and Discussion Genome mining of LanM enzymes’ sequence diversity to