Ni-promoted reductive cyclization cascade enables a total synthesis of (+)-aglacin B

• Si-Chen Yao,
• Jing-Si Cao,
• Jian Xiao,
• Ya-Wen Wang and
• Yu Peng

Beilstein J. Org. Chem. 2025, 21, 2548–2552, doi:10.3762/bjoc.21.197

• single crystals, and a corresponding X-ray diffraction analysis (inset in Scheme 3, selected H atoms have been omitted for clarity, and Table S3, Supporting Information File 1) unambiguously confirmed its precise structure with three continuous chiral centers. Conclusion In summary, the total synthesis

Insoluble methylene-bridged glycoluril dimers as sequestrants for dyes

• Suvenika Perera,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 2302–2314, doi:10.3762/bjoc.21.176

• methyl substituents (H2). Fortunately, the X-ray crystal structures of G2W1 and G2W3 reported below shed further light on their poor performance as solid state sequestrants. X-ray crystal structure of G2W1 and G2W3 Eventually, we were able to grow single crystals of G2W3 (CCDC 2466611) and solve their

• substituents – provides a compelling explanation for the superior performance of H2 over G2W3 and G2W4. We were also fortunate to obtain single crystals of G2W1 (CCDC 2466610) and solve the structure by X-ray diffraction measurements. Crystals of G2W1 are triclinic with the P−1 space group (a/Å = 15.414(4); b

A m-quaterphenyl probe for absolute configurational assignments of primary and secondary amines

• Yuka Takeuchi,
• Mutsumi Kobayashi,
• Yuuka Gotoh,
• Mari Ikeda,
• Yoichi Habata,
• Tomohiko Shirai and
• Shunsuke Kuwahara

Beilstein J. Org. Chem. 2025, 21, 2211–2219, doi:10.3762/bjoc.21.168

• configurations of both natural and synthetic compounds continues to pose a considerable challenge in the life and materials sciences [1]. While X-ray crystallography remains a reliable method for this purpose, the requirement for high-quality single crystals often limits its applicability. In recent years

Multicomponent reactions IV

• Thomas J. J. Müller and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2082–2084, doi:10.3762/bjoc.21.163

• Thomas J. J. Muller Valentyn A. Chebanov Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie, Universitätsstraße 1, D-40225 Düsseldorf, Germany Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of

• is guest-edited by Thomas J. J. Müller (Heinrich Heine University Düsseldorf, Germany) together with Valentyn A. Chebanov (State Scientific Institution “Institute for Single Crystals” of the National Academy of Sciences of Ukraine, Kharkiv, Ukraine). The 30 contributions collected in this thematic

Switchable pathways of multicomponent heterocyclizations of 5-amino-1,2,4-triazoles with salicylaldehydes and pyruvic acid

• Yana I. Sakhno,
• Oleksander V. Buravov,
• Kostyantyn Yu. Yurkov,
• Anastasia Yu. Andryushchenko,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2030–2035, doi:10.3762/bjoc.21.158

• Yana I. Sakhno Oleksander V. Buravov Kostyantyn Yu. Yurkov Anastasia Yu. Andryushchenko Svitlana V. Shishkina Valentyn A. Chebanov Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky Ave., 60

α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

• Vladyslav O. Honcharov,
• Yana I. Sakhno,
• Olena H. Shvets,
• Vyacheslav E. Saraev,
• Svitlana V. Shishkina,
• Tetyana V. Shcherbakova and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

• Vladyslav O. Honcharov Yana I. Sakhno Olena H. Shvets Vyacheslav E. Saraev Svitlana V. Shishkina Tetyana V. Shcherbakova Valentyn A. Chebanov Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky

Synthesis of N-doped chiral macrocycles by regioselective palladium-catalyzed arylation

• Shuhai Qiu and
• Junzhi Liu

Beilstein J. Org. Chem. 2025, 21, 1917–1923, doi:10.3762/bjoc.21.149

• characterized by NMR spectroscopy, mass spectrometry, and X-ray crystallography. Single crystals suitable for X-ray diffraction measurements of compounds 3a, MC2, and MC3 were successfully obtained to reveal their molecular structures. In the crystal structure of 3a (Figure 2a), the two pyrene units are nearly

Preparation of spirocyclic oxindoles by cyclisation of an oxime to a nitrone and dipolar cycloaddition

• Beth L. Ritchie,
• Alexandra Longcake and
• Iain Coldham

Beilstein J. Org. Chem. 2025, 21, 1890–1896, doi:10.3762/bjoc.21.146

• rate of evaporation from a nanolitre solution of analyte encased within oil [33], suitable single crystals were obtained. The X-ray analysis allowed the determination of the relative stereochemistry, as shown in Figure 2. Compound 5a crystallised as a racemic mixture in the space group P21/c. The major

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• , Shibaura Institute of Technology, 307 Fukasaku, Minuma-ku, Saitama 337-8570, Japan 10.3762/bjoc.21.138 Abstract In single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one and the thione analogue, a unique association based on a halogen–π interaction was detected. In racemic and optically pure

• ; single crystals; thiones; Introduction In the past several years, C–N atropisomers (C–N axially chiral compounds) owing to the rotational restriction around a C–N single bond have received great attention as new target molecules for catalytic asymmetric reactions. Highly enantioselective syntheses of

• the single crystals of racemates significantly differs from that of optically pure forms (chirality-dependent halogen bonding, Figure 1) [20][21]. That is, in crystals of racemic mebroqualone rac-I, heterochiral zig-zag polymer chains, in which (P)-I and (M)-I were alternately connected, were formed

Synthesis of an aza[5]helicene-incorporated macrocyclic heteroarene via oxidation of an o-phenylene-pyrrole-thiophene icosamer

• Yusuke Matsuo,
• Aoi Nakagawa,
• Shu Seki and
• Takayuki Tanaka

Beilstein J. Org. Chem. 2025, 21, 1561–1567, doi:10.3762/bjoc.21.119

• and 8.98 ppm and five doublet signals due to the heterole β-protons in the range of 6.7–5.8 ppm, along with o-phenylene protons around 7 ppm. Single crystals suitable for X-ray diffraction analysis were obtained from a mixture of acetone/n-hexane and the solid-state structure was successfully

Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones

• Grzegorz Mlostoń,
• Małgorzata Celeda,
• Marcin Palusiak,
• Heinz Heimgartner,
• Marta Denel-Bobrowska and
• Agnieszka B. Olejniczak

Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113

• analysis (Figure 1a and Figure 1b, respectively). Single crystals of 9i and 10i were obtained by slow evaporation from a hexane/CH2Cl2 solution and subsequently used for crystallographic X-ray measurements. In the case of 9i, the molecule is strongly disordered in the outer carbon ring regions. However

Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes

• Bartłomiej Pigulski

Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99

• non-benzenoid nanographene 34 [45]. Single crystals of 34 surprisingly exhibit SHG-CD (second harmonic generation–circular dichroism) properties due to the unusual self-sorting of R and S enantiomers in the crystalline state. Scholl-type oxidation: The Scholl oxidation is a highly useful tool for

Synthetic approach to borrelidin fragments: focus on key intermediates

• Yudhi Dwi Kurniawan,
• Zetryana Puteri Tachrim,
• Teni Ernawati,
• Faris Hermawan,
• Ima Nurasiyah and
• Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

• LiAlH4 in ether to form alcohol 40 (89%) (Scheme 3). The primary alcohol 40 was then converted to its iodide derivative 42 (89%), from which single crystals were obtained, and its structure was determined unequivocally by XRD crystallography. Iodide 42 was then reacted with sodium phenylsulfinate in DMF

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

• diffraction of single crystals (Figure 3), showing, for both 1:1 and 2:1 stoichiometries, cyanoaurate anions inside the host cavity and potassium cations interacting with hydroxy groups of adjacent cyclodextrins. The strong host–guest affinity and complex stability in the solution phase has been studied by

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

• Krishna Pandey,
• Lucas X. Orton,
• Grayson Venus,
• Waseem A. Hussain,
• Toby Woods,
• Lichang Wang and
• Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

• Information File 1. Single crystals with quality suitable for XRD analysis were obtained in both cases (Figure 5). Unlike the previous assumption of metal coordination at the macrocycle core [17], the crystal structures reveal complexation of both cations at the periphery of the macrocycle. Both 1/LiBArF20

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

• target ultracyclic hosts. The synthesized ultracycles were fully characterized by spectrometric and elemental analysis (Scheme 1 and Schemes S1‒S3 in Supporting Information File 1). Single crystals of B4aH were obtained by slow vapor diffusion of ethyl ether into an acetonitrile/chloroform 1:1 (v/v

Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation

• Zhihua Liu,
• Ya-Zhi Chen,
• Ji Wang,
• Qingling Nie,
• Wei Zhao and
• Biao Wu

Beilstein J. Org. Chem. 2025, 21, 845–853, doi:10.3762/bjoc.21.68

• understand cooperative interactions between complexed ions, we tried to grow the crystal structure of studied salts. Fortunately, single crystals of Cs2CO3 and Cs3PO4 complexes were obtained by slow vapor diffusion from acetonitrile and diethyl ether. Notably, clearly stronger ion-dipole interactions of

Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups

• Christian Akakpo,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55

• hydrophobic region of the guest which changes the orientation of Ha with respect to the magnetically shielding region [54][63][64]. X-ray crystal structure of C1 We were fortunate to obtain single crystals of the C1·Me6CHDA complex and solved the crystal structure by X-ray diffraction (CCDC 2411723). Figure 5

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

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• spectroscopy (Scheme 1). During the reaction progress, the C=C bonds of bpe ligands undergo pedal-like motion prior to photodimerization [63]. For the single-crystal irradiation, the slow reactivity can be attributed to the hindered pedal motion in the single crystals, likely due to the presence of

• -dichlororesorcinol (2.2) in the solid state (Scheme 2) [64]. The authors noticed that single crystals of 2.1·2.2 (1:1 stoichiometry) produced by mortar-and-pestle grinding undergo a single-crystal-to-single-crystal (SCSC) transformation when exposed to UV light (medium-pressure Hg lamp). The cyclobutane 2.3 was

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

• Kirill A. Gomonov,
• Vasilii V. Pelipko,
• Igor A. Litvinov,
• Ilya A. Pilipenko,
• Anna M. Stepanova,
• Nikolai A. Lapatin,
• Ruslan I. Baichurin and
• Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

• phase and visualized under UV light (λ 254 nm). X-ray structure determination X-ray diffraction studies of single crystals of compounds 5a, 5b, 6b, 6c, and 7a were carried out on a Bruker D8 QUEST diffractometer. The cell parameters and experimental data were obtained at 100 K (graphite monochromator

• structural analysis were obtained by crystallization from MeOH (5a), EtOH (5b), or DMFA (6b, 6c, and 7a). Single crystals of a suitable size were glued to the top of a glass fiber in a random orientation. The preliminary unit cell parameters were determined using three runs at different ω angle positions

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

• the resonance of the internal aromatic protons Ha and Hb in the host H (Δδ= −0.170 and +0.218 ppm, respectively), which all pointed toward the existence of strong host–guest interactions in solution. Then we attempted to grow single crystals of the complex out of curiosity, wondering whether the 2:2

• structure would also be found in the solid state. Fortunately, single crystals of the complex H1 ⊃ G1 were obtained by slow evaporation of chloroform/acetone solvent (1:1, v/v) into a small amount of methanol over the course of two weeks. Indeed, analysis of the crystal structure of the complex revealed a

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

• than the colorless crystal of Cs-1. Slow evaporation of solvent from a solution of 3 in CH2Cl2/CH3OH resulted in the formation of single crystals suitable for X-ray crystallography [27]. Compound 3 consists of three [5]helicenoid moieties, with two of them containing three benzene rings, one five

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

• ) was prepared to grow single crystals suitable for X-ray analysis (Scheme S2 in Supporting Information File 1) in order to confirm the annulation reaction pattern, and 2,3,6,7-tetrakishexyloxy-10-phenyltriphenylene (BTP6, Scheme S3), the non-fluorinated isomer of F6 and PH6 (Figure 1), for probing the

• analysis (Figures S1–S32, Supporting Information File 1), and all the results agree with the proposed molecular structures. Single-crystal structure of F Suitable single crystals of compound F for X-ray analysis were obtained by slow evaporation of an ethyl acetate/ethanol solution (Figure 2, and

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

• of oxalate is an order of magnitude higher than the one of acetate and benzoate which is in line with the fact that oxalate is supposed to be pinched between both zinc centers while the monocarboxylates coordinate only to one zinc atom. Unfortunately, we could not grow suitable single crystals of