Recent advances in controllable/divergent synthesis

• Jilei Cao,
• Leiyang Bai and
• Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

• successfully applied in the synthesis of complex natural products, pharmaceuticals, and functional materials, often streamlining multistep sequences and minimizing protecting-group strategies [50][51]. In 2016, Li and co-workers developed divergent coupling conditions for iminamides 77 with receptor-type diazo

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

• ]. Additionally, dicarboxylates like tartrate, adipate or citrate are widely used as food additives [23][24]. Furthermore, functional materials based on dicarboxylates are expected to play a significant role in future technologies [25]. Therefore, the recognition and detection of dicarboxylates are of great

Origami with small molecules: exploiting the C–F bond as a conformational tool

• Patrick Ryan,
• Ramsha Iftikhar and
• Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

• Yuuki Ishii,
• Minoru Yamaji,
• Fumito Tani,
• Kenta Goto,
• Yoshihiro Kubozono and
• Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53

• due to the angular annelation. These series are known as one-dimensional graphene ribbons. As has been commonly recognized, acene molecules have been intensively and extensively studied in the organic functional materials field [5][6][7]. By contrast, phenacenes had been hardly applied as functional

• the manipulation of the solid-state optoelectronic nature of polycyclic aromatic molecules to develop future functional materials in organic electronics. Chemical structures of phenacenes studied in this work. UV–vis and fluorescence spectra of F8PIC (a), F8FUL (b), and F87PHEN (c) (red lines) and the

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

• Zahra Noori,
• Miquel Solà,
• Clara Viñas,
• Francesc Teixidor and
• Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

• , exceptional thermal and chemical stability, and robust synthetic versatility [16][17] – make carborane derivatives essential components in various fields. These include pharmaceuticals [18][19][20][21][22], boron neutron capture therapy (BNCT) [23][24][25][26], organometallic ligands [27], and functional

• materials [28][29][30]. As a result, developing efficient methods for selectively introducing functional groups into carboranes has become a key area of research [29][31]. Moreover, replacing planar aryl rings in biologically active molecules with spherical carborane units has led to novel alternatives [32

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

• polymerization concentration of 17 μM. These polymers were highly concentration-dependent. Establishing this new dimerization motif with shape-persistent H-bonded macrocycles widens the scope of noncovalent building blocks for supramolecular polymers and augurs well for the future development of functional

• materials. Keywords: hydrogen-bonded macrocycle; orthogonal self-assembly; shape-persistent; supramolecular polymer; Introduction Host–guest interactions, particularly those involving macrocycles as hosts [1], have found a myriad of applications in supramolecular chemistry [2][3][4] owing to their ability

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

• expand this chemistry, enabling access to new π-extended molecular systems that might be challenging to synthesize through conventional synthetic routes. This dual focus highlights the study’s potential to advance both the design of functional materials and the development of innovative synthetic

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

• palladium catalyzed C–H arylation to pyridine derivatives. The cyclization reaction proceeded in a moderate to excellent yield when an appropriate phosphine ligand was employed. The reaction is expected to be useful for the synthesis of functional materials, and bioactive molecules in a facile manner

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

• Sergio Torres-Oya and
• Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

• imines; asymmetric organocatalysis; cyclization; N-heterocycles; inverse electron demand aza-Diels–Alder reaction; Introduction Nitrogen-containing heterocycles are abundant scaffolds present in natural products, biologically active compounds, pharmaceuticals, synthetic agrochemicals, and functional

• materials [1][2]. Due to their importance, different synthetic routes involving stoichiometric and catalytic approaches have been developed. The α,β-unsaturated imines, also known as conjugated imines or 1-azadienes, are useful precursors for the construction of aza-heterocycles. Due to their structure

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

• or fluoroalkyl motifs into organic molecules or key frameworks stands out as a crucial and appealing approach in uncovering and crafting innovative drugs, agrochemicals, and functional materials (Figure 1) [1][2][3][4]. Fluorinated functional groups can positively alter the electronic characteristics

Mechanochemical difluoromethylations of ketones

• Jinbo Ke,
• Pit van Bonn and
• Carsten Bolm

Beilstein J. Org. Chem. 2024, 20, 2799–2805, doi:10.3762/bjoc.20.235

• through the formation of novel reactive intermediates [15][16][17][18]. Fluorine-containing functional groups are essential structural motifs in the development of new bioactive compounds and functional materials. Compared to their non-fluorinated analogs, the presence of fluorine atoms in molecular

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

• the aid of intermolecular C–H···π interactions. Such characteristic anion-driven assemblies of TATA+ are not known, and further studies on ion-pairing assemblies of modified TATA+ can lead to the development of functional materials, comprising multiple components associated via iπ–iπ interactions that

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

• manner, and from the few reports using 2-bromoresorcinol, it has been described to yield inseparable mixtures of oligomers [9][59]. Electron-withdrawing groups like carboxylic acids are another useful functional group instead of the halogen that provide a divergent route to other functional materials

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

• Naoki Takeda,
• Shuichi Akasaka,
• Susumu Kawauchi and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

• ] cycloaddition–retroelectrocyclization (CA-RE) between electron-rich alkynes and electron-deficient olefins [8]. The [2 + 2] CA-RE click reactions were employed to produce a variety of functional materials, such as nonlinear optical chromophores [9][10], super acceptors [11][12], ion sensing D–A systems [13

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

• functional materials for diverse uses [1][5][6][7]. Notably, to synthesize this vital heptacyclic star‐shaped π‐conjugated polyarene framework, only a single acid-mediated co-trimerization step is required from an inexpensive and commercially available starting material, namely 1-indanone [8]. It is to be

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• Alexander V. Tsygankov Vladyslav O. Vereshchak Tetiana O. Savluk Serhiy M. Desenko Valeriia V. Ananieva Oleksandr V. Buravov Yana I. Sakhno Svitlana V. Shishkina Valentyn A. Chebanov Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

• Ka-Lung Hung,
• Leong-Hung Cheung,
• Yikun Ren,
• Ming-Hin Chau,
• Yan-Yi Lam,
• Takashi Kajitani and
• Franco King-Chi Leung

Beilstein J. Org. Chem. 2024, 20, 1590–1603, doi:10.3762/bjoc.20.142

• photochromic systems and smart functional materials [47][49][50][51][52][53][54][55][56][57][58][59]. Inspired by the molecular designs of DASAs, we developed the first DASA amphiphiles (DAs) assembled into large-aspect-ratio nanostructures in aqueous medium while sustaining the visible-light-controlled

Synthesis of cyclic β-1,6-oligosaccharides from glucosamine monomers by electrochemical polyglycosylation

• Md Azadur Rahman,
• Hirofumi Endo,
• Takashi Yamamoto,
• Shoma Okushiba,
• Norihiko Sasaki and
• Toshiki Nokami

Beilstein J. Org. Chem. 2024, 20, 1421–1427, doi:10.3762/bjoc.20.124

• polymerization of organic molecules is an important strategy for the preparation of functional materials, such as conducting polymers [1][2][3][4][5]. Electrochemical reactions can be controlled by electric potential or current, electrodes, and electrolytes, which are not available in conventional chemical

Challenge N- versus O-six-membered annulation: FeCl₃-catalyzed synthesis of heterocyclic N,O-aminals

• Giacomo Mari,
• Lucia De Crescentini,
• Gianfranco Favi,
• Fabio Mantellini,
• Diego Olivieri and
• Stefania Santeusanio

Beilstein J. Org. Chem. 2024, 20, 1412–1420, doi:10.3762/bjoc.20.123

• natural products, pharmaceuticals, and functional materials (Figure 1) [1][2][3]. It has been assessed that almost one-third of the best-selling therapeutics contains fused heterocyclic structures [4]. Among the N-heterocycles, imidazopyrazine structures [5][6], derived from amalgamation of privileged

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• ][51]. Based on a SciFinder® survey, we came to realise that a small number of aryl-cored dibromides, which can be derived from xylenes (1, 2, 3) or mesitylene (4, Figure 3), play a predominant role as building blocks for the construction of functional materials and/or polymeric architectures. Some

Spin and charge interactions between nanographene host and ferrocene

• Akira Suzuki,
• Yuya Miyake,
• Ryoga Shibata and
• Kazuyuki Takai

Beilstein J. Org. Chem. 2024, 20, 1011–1019, doi:10.3762/bjoc.20.89

• depletion, is attracting much attention due to its potential for creating a new class of functional materials with various guest molecules [1]. In particular, nanosized graphene called nanographene, the macroscopic limit of polycyclic aromatic hydrocarbon molecules, is a magnetic host material with spins

One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

• Jiawei Niu,
• Yuhui Wang,
• Shenghu Yan,
• Yue Zhang,
• Xiaoming Ma,
• Qiang Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

• [10][11] (Figure 1). The tetrazole ring can also be found in functional materials for photography, imaging, and military applications [12][13][14][15][16][17]. The hydroisoquinoline core, such as 1,2,3,4-tetrahydroisoquinoline and pyrazino[2,1-a]isoquinolinone, is also a privileged heterocycle which

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

• Ke Jiang,
• Cheng Pan,
• Limin Wang,
• Hao-Yang Wang and
• Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

• for the synthesis of functional materials via cross-coupling reactions. Next, we extended our investigation to 1-naphthol in this reaction, and found that the arylation of 1-naphthol was achieved selectively at the C-2 position. The cascade cyclization resulted in the corresponding products 3an and

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• and used in medicine, food industry, catalysts, dyes, functional materials, oil refining, and electronics [1][2]. Quinoline and its derivatives have antibiotic, antimalarial, antitumor, anti-inflammatory, antihypertensive, and antiretroviral properties [3][4]. Therefore, at present, there is a need

Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• Over the past decades, the 8-aminoquinoline motif that could be found in several natural products [1] has attracted significant attention for its widespread usage in pharmaceuticals [2], agrochemicals [3], and functional materials [4]. In particular, the aminoquinoline scaffold has emerged as an