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

• concentrations used for ANTH, 9,10-ANTH(BnF)2, and quinine sulfate were 1.89, 1.14, and 1.94 (10−5 M), respectively. Relative quantum yields were calculated using the following equation referenced to quinine sulfate (Φf = 0.55 in 0.1 M H2SO4): X-ray crystallography The diffraction-quality single crystals of 9

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

• Metodej Dvoracek,
• Brendan Twamley,
• Mathias O. Senge and
• Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

• promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation. Keywords: bimane; [2 + 2] cycloaddition; fluorescence; topochemical polymerization; X-ray crystallography; Introduction Topochemical polymerizations refer to polymerization reactions occurring in the

Electrochemical synthesis of cyclic biaryl λ³-bromanes from 2,2’-dibromobiphenyls

• Andrejs Savkins and
• Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

• extractive workup followed by reversed-phase chromatography and its structure was unambiguously confirmed by X-ray crystallography (Table 1, graphic). Gratifyingly, a two-fold increase in the yield was achieved by a slight reduction of the current density to j = 8 mA·cm−2 (entry 2 vs entry 1 in Table 1). A

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

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

• literature. During our attempt to scale up the preparation of BPP 2 through the "DPEX" reaction, we unexpectedly obtained a 5-isopropoxy-substituted derivative of BPP (BPP-OiPr 3) (Scheme 1), whose structure was proven by NMR, mass spectrometry, and X-ray crystallography. In this work, we optimized the

• 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

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

• structure of 16 was confirmed by serial X-ray crystallography using an X-ray free-electron laser (XFEL) [deposition number CCDC 2352718) [54][55]. We then performed a Strecker-type reaction on the aldehyde 16 to construct an α-aminonitrile 17. To our delight, the key intermediate, 2,3-diaminobenzofuran 11

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

• analysis of it with X-ray crystallography. Interestingly, it is observed that tris(4,5-dehydro-2,3:6,7-dibenzotropone) crystallized from its solution in hexane resulting in colorless and yellow crystal polymorphs, where it adopts conformations of approximate Cs and C2 symmetry, respectively. Furthermore

•  1) featuring three heptagons and two pentagons, with its structure confirmed by X-ray crystallography. This π-expansion approach of compound 1 differs from the method reported by Müllen and co-workers, which involves Ramirez olefination and Suzuki coupling, resulting in the expansion of a seven

• Scholl reaction conditions. The structure of 3 was confirmed with single crystal X-ray crystallography, as detailed later. In addition, another product with a molecular ion peak of 1695.9115 in the high-resolution mass spectrum (Supporting Information File 1, Figure S6) was isolated in trace amounts

Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives

• Shuxian Qiu,
• Duan Dong,
• Jiahui Li,
• Huiting Wen,
• Jinpeng Li,
• Yu Yang,
• Shengxian Zhai and
• Xingyuan Gao

Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274

• fully elucidated by single-crystal X-ray crystallography, which was performed on a Bruker APEX-II CCD diffractometer using graphite monochromated Mo Kα radiation at a temperature of 296 ± 2 K. Crystallographic data were deposited with the Cambridge Crystallographic Data Centre under accession number

Hypervalent iodine-mediated intramolecular alkene halocyclisation

• Charu Bansal,
• Oliver Ruggles,
• Albert C. Rowett and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

• excellent yields. The structures were also assigned by X-ray crystallography. Sulfur nucleophiles In 2015, Li and co-workers reported the synthesis of 5-bromomethyl-2-phenylthiazoline (79, Scheme 41) [48]. Sulfur was used as the internal nucleophile instead of nitrogen, as previously reported by the authors

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

• polar mixture Host 2 it is twice as high as for less polar Host 1. Selected examples of chiral dopants with high HTPs in their nematic host LC mixture. Configuration of (R,R)-3 determined by X-ray crystallography. Configuration of (R,R)-4 determined by X-ray crystallography. Structure–property

Structure and thermal stability of phosphorus-iodonium ylids

• Andrew Greener,
• Stephen P. Argent,
• Coby J. Clarke and
• Miriam L. O’Duill

Beilstein J. Org. Chem. 2024, 20, 2931–2939, doi:10.3762/bjoc.20.245

• to fully understand the electronic effect of the arene substituent. Conclusion A systematic investigation of phosphorus-iodonium ylids was carried out, correlating structural data from X-ray crystallography with thermal stability data from DSC and TGA measurements. A common decomposition mechanism

C–C Coupling in sterically demanding porphyrin environments

• Liam Cribbin,
• Brendan Twamley,
• Nicolae Buga,
• John E. O’ Brien,
• Raphael Bühler,
• Roland A. Fischer and
• Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

• porphyrins appended with boronic ester groups to be structurally disseminated by X-ray crystallography [62][63]. Compound 46 was found to crystallize in a 1:1 ratio with bis(pinacolato)diboron, with a void size of 8–9 Å. The formation of channel-type lattice structures is thermodynamically unfavorable, when

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

• Connor R. M. MacDonald and
• Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

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

• donors in recent years. Herein, a new structural motif for this compound class was developed: iodoloisoxazolium salts, bearing a cyclic five-membered iodolium core fused with an isoxazole ring. A derivative of this class was synthesized and investigated in the solid state by X-ray crystallography

Asymmetric organocatalytic synthesis of chiral homoallylic amines

• Nikolay S. Kondratyev and
• Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

• enantioselectivities were in the range of 82–97% and were lowest for the prenylation, and highest for Z-geranylboronic acid. The absolute configurations of the products were established by X-ray crystallography of the hydrochloride salts of the corresponding bromoindole and bromodihydroisoquinoline derivatives 20 and

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

• , Supporting Information File 1). ESR and MS measurements as well as X-ray crystallography revealed that the radical species was assigned 10-mesityl-9-anthroyxyl radical (5), obtained in 47% yield (Figure 4c, Figure S8, Supporting Information File 1). Thus, two decomposition pathways were considered: a minor

• . 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

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• needed to deeply investigate the multifaceted aspects of protein–glycan interactions. To date, advanced and versatile NMR, X-ray crystallography, and MS methods [36][37][38] above all, have been developed to reach extensive information on the structural and conformational features of glycans and proteins

• . Several experimental techniques, including NMR, X-ray crystallography and Cryo-EM, can provide critical information for the characterisation of protein structure and conformation. Their widespread and wisely use permitted to experimentally determine the structures of around 200,000 proteins [78], all

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

• Scheme 1 compound 6 was treated with isopropyl iodide (7) in DMF in the presence of sodium hydride to provide products 8 and 9 in 38% and 46% yields, respectively. The structures of both compounds were unambiguously assigned using X-ray crystallography and 1H and nuclear Overhauser effect (NOE) NMR

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• (1–3 % spectroscopic yield) when BF3·OEt2 was added to the reaction mixture. X-ray crystallography and DFT calculations The solid-state structure of difluoroiodane 6 is shown in Figure 2 and displays the expected square pyramidal geometry around the iodine atom, with only minor distortion (τ5 = 0.191

Synthesis and characterization of 1,2,3,4-naphthalene and anthracene diimides

• Adam D. Bass,
• Daniela Castellanos,
• Xavier A. Calicdan and
• Dennis D. Cao

Beilstein J. Org. Chem. 2024, 20, 1767–1772, doi:10.3762/bjoc.20.155

• cyclic imides. The solid-state structures of the N-phenyl derivatives, determined by X-ray crystallography, reveal changes in packing preference based on the number of aromatic rings in the core. The optical and electronic properties of the title compounds compare favorably with other previously

• evaporation of CH2Cl2/MeOH solutions and characterized by X-ray crystallography. 7-Ph crystallizes in the Pbcn space group into a solvent superstructure of π-stacked columns of 7-Ph. The imide groups are pointed in alternating directions within a stack. While this may occur in part as a consequence of the

• -Ph as determined by X-ray crystallography. Representative C=O···H–C and C–H···π interactions are indicated in teal and magenta, respectively. Top-down views of π-stacking modes in c) 7-Ph and d, e) 8-Ph. Hydrogen atoms have been removed for clarity in c–e. Atom color code: C = tan, H = white, Cl

Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones

• Pooja Goyal,
• Akhil K. Dubey,
• Raghunath Chowdhury and
• Amey Wadawale

Beilstein J. Org. Chem. 2024, 20, 1518–1526, doi:10.3762/bjoc.20.136

• center. Under the disclosed optimized conditions, the product ent-3ba was isolated as white solid with 85% ee and the enantiopurity of the product could be enriched to 98% ee by single recrystallization. The absolute stereochemistry was determined to be “R” on the basis of single-crystal X-ray

• crystallography data of ent-3ba (Figure 2) [37]. The stereochemistry of the products in this series was assigned by analogy. Based on the observed absolute configuration of product ent-3ba and preceding literature reports [38][40], a plausible mechanistic pathway is outlined in Scheme 5. Initially, in the

Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines

• Stefan Jopp,
• Franziska Spruner von Mertz,
• Peter Ehlers,
• Alexander Villinger and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1246–1255, doi:10.3762/bjoc.20.107

• group, could not be isolated at all, since the reaction resulted in an inseparable mixture of several products. The structure of 6b could be independently confirmed by X-ray crystallography (Figure 2). Both phenyl rings are found to be twisted in an angle of approximately 45° from the quinoline core. As

• the 6-position in comparison to the 8-position. The structure of product 9f was confirmed by X-ray crystallography (Figure 3). The thiophene ring in 4-position is in plane with the quinoline core, while the other ring is twisted in an angle of approximately 85°. This might be explained by an

• dehalogenation at position 3. In particular, the side-product 6b was isolated in 25% yield during the purification of 12b. The structure of product 12d was proven by X-ray crystallography (Figure 4). All three phenyl rings are found to be nearly in plane with the quinoline core, showing only a slight twist of 5

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• , and methyl anthranilate, with selenium dioxide in acetonitrile. A systematic analysis of the reaction products with the help of 77Se NMR and single-crystal X-ray crystallography revealed that the reaction progress follows three major reaction pathways, electrophilic selenation, oxidative

Introduction of peripheral nitrogen atoms to cyclo-meta-phenylenes

• Koki Ikemoto and
• Hiroyuki Isobe

Beilstein J. Org. Chem. 2024, 20, 1207–1212, doi:10.3762/bjoc.20.103

• nitrogen-doped [n]CMPs (3) containing outward-radiating nitrogen dopants. The properties and structures were investigated with UV–vis spectroscopy and X-ray crystallography, which revealed the fundamental properties of the nitrogen dopants in the macrocyclic structures. Results and Discussion Nitrogen

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

• Masahiro Kako,
• Masato Kai,
• Masanori Yasui,
• Michio Yamada,
• Yutaka Maeda and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100

• -silylene adduct 3 of C60 based on spectroscopic measurements, X-ray crystallography, electrochemical analyses, and theoretical calculations. Results and Discussion Synthesis of bis-silylene adduct 3 The synthesis of the silylene adduct was conducted using a modified literature procedure [15]. A degassed

• (s, 1C), 37.59 (d, 2C), 37.35 (d, 2C), 37.24 (d, 2C), 37.11 (d, 2C), 28.55 (q, 2C), 27.86 (q, 2C), 27.57 (q, 2C), 27.44 (q, 2C), 25.61 (q, 2C), 25.25 (q, 2C), 25.10 (q, 2C), 24.11 (q, 2C); UV–vis (CH2Cl2) λmax 515 nm. X-ray crystallography of 3: Black plate crystals suitable for X-ray diffraction