Visible-light-driven NHC and organophotoredox dual catalysis for the synthesis of carbonyl compounds

• Vasudevan Dhayalan

Beilstein J. Org. Chem. 2025, 21, 2584–2603, doi:10.3762/bjoc.21.200

• cycloalkanone scaffolds with potential applications in pharmaceutical and materials sciences (Scheme 12) [62]. Sumida, Ohmiya, and co-workers recently developed an NHC-and organic photoredox-catalyzed meta-selective Friedel–Crafts type acylation of electron-rich aromatic compounds 31. The described catalytic

C2 to C6 biobased carbonyl platforms for fine chemistry

• Jingjing Jiang,
• Muhammad Noman Haider Tariq,
• Florence Popowycz,
• Yanlong Gu and
• Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

• dedicated to the conversion of biomass-derived platform molecules [10][11]. Recent studies have also highlighted the potential of biobased aromatic compounds as sustainable alternatives to their fossil-derived counterparts [12][13][14][15]. Developing biobased solvents [16][17] and platform chemicals from

Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules

• Wei Liu and
• Xiaoyu Yang

Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145

• reaction mechanisms and applications of the chiral products for selected examples. Review Helical chirality Helicenes are a group of rigid polycyclic aromatic compounds composed of ortho-fused aromatic (hetero)cyclic rings, with their helically twisted conformation enforced by steric hindrance between

Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade

• Feng Zhou,
• Chuansong Duanmu,
• Yanxing Li,
• Jin Li,
• Haiqing Xu,
• Pan Wang and
• Kai Zhu

Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132

• development of continuous-flow nitration processes, offering researchers a consolidated reference for process optimization and system design. Applications of flow chemistry in nitration reactions have predominantly focused on aromatic compounds (89% in Table S1 in Supporting Information File 1, vs 11% for

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

• Jiangfei Chen,
• Yi-Lin Qu,
• Ming Yuan,
• Xiang-Mei Wu,
• Heng-Pei Jiang,
• Ying Fu and
• Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

Recent advances in the electrochemical synthesis of organophosphorus compounds

• Babak Kaboudin,
• Milad Behroozi,
• Sepideh Sadighi and
• Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

• reaction proceeded with electrophilic iodination of aromatic compounds followed by a nucleophilic reaction of the formed phosphorothioate intermediate to give corresponding S-heteroaryl phosphorothioates in good to excellent yields (Scheme 29). In 2023, Liu et al. [70] reported an interesting

• occurrence of this rearrangement. Electrochemical Se–P bond formation In another study, Gu et al. [71] reported electrochemical P–Se bond formation of the reaction of elemental Se with diethyl phosphonate and aromatic compounds. In this method, potassium iodide acts as a key additive. The reaction is carried

• , followed by the iodination reaction of aromatic compounds (Scheme 31). In the next step, elemental selenium was inserted into the aryl iodide bond to form the aryl iodoselenide intermediate for forming the P–Se bond. Other electrochemical reactions of organophosphorus Li et al. [72] reported an

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

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

• new, structurally-related series of π-conjugated aromatic compounds (Figure 1) based on a simple triphenylene core and evaluating the mesomorphic and optical properties. Specifically 1,2,4-trifluoro-6,7,10,11-tetraalkoxy-3-(perfluorophenyl)triphenylenes (Fn, Figure 1), bearing a terminal fluoroarene

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

• Bhaskar B. Dhotare,
• Seema V. Kanojia,
• Chahna K. Sakhiya,
• Amey Wadawale and
• Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

• reported over the years (Figure 2) [2]. Conventionally, benzophenones are synthesized by Friedel–Crafts acylation of benzoyl halides and aromatic compounds. However, the regioselectivity of Friedel–Crafts benzoylation at the desired position is difficult to control [9]. On the other hand, 2

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

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

• described isomers and expand the toolbox of electron-deficient aromatic compounds available to organic materials chemists. Keywords: electron acceptors; organic materials; polycyclic aromatic hydrocarbons; Introduction Aromatic diimides are ubiquitous molecular scaffolds that have served as the basis for

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

• interest [12][13]. The various approaches used for selenation of aromatic compounds include directed lithiation [14][15], copper-catalyzed selenation [16][17][18], and aromatic nucleophilic substitution reactions [19][20][21][22]. Electrophilic selenium reagents (e.g., phenylselenenyl bromide) have often

• , regioselective aromatic electrophilic substitution is often difficult. Various synthetic strategies have evolved to address such problems and expand the scope of SeO2 beyond the oxidizing capability. Ren et al. adopted potassium-iodide-mediated catalytic selenation of aromatic compounds using SeO2 (Scheme 1) [33

• . Computationally optimized structure of aniline (a), o-anisidine (b), and methyl anthranilate (c), with atom labels indicated. Reported synthetic methods for the selenation of aromatic compounds. Reaction of selenium dioxide with aniline. Reaction of selenium dioxide with o-anisidine. Reaction of methyl

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• industries [83][84][85]. Various manganese catalysts have been reported (Figure 4) for the C-alkylation of heterocyclic compounds with several alcohols, including indoles and quinolines. In 2017, Kirchner’s group established a new method for the aminomethylation of aromatic compounds with secondary amines

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

• this approach. Arylation reactions of aromatic compounds and reaction patterns of ortho-functionalized diaryliodonium salts. Mechanism study. Standard conditions: 1 (0.3 mmol, 1 equiv), 2 (0.33 mmol, 1.1 equiv), Cu(OAc)2 (10 mol %), DCE (2 mL), 80 °C, 3 hours. TEMPO = 2,2,6,6-tetramethylpiperidine-1

Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus

• Dongxu Zhang,
• Wenyu Du,
• Xingming Pan,
• Xiaoxu Lin,
• Fang-Ru Li,
• Qingling Wang,
• Qian Yang,
• Hui-Min Xu and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2024, 20, 815–822, doi:10.3762/bjoc.20.73

• biocatalysts, capable of catalyzing a wide range of reactions and processing a variety of substrates [35][36]. They effectively recognize different structural types, including aromatic compounds, polyketides, terpenes, peptides, and carbohydrates [37][38][39][40]. To investigate the substrate spectrum of CavA

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• this situation. Acenes are a class of aromatic compounds composed of linearly fused benzene rings, which can be regarded as the narrowest graphene nanoribbons. They are highly promising p-type organic semiconductors, but suffer from insolubility and instability leading to dimerization and/or

• , and this reactivity pattern was exploited as early as in the 1950s to generate in a controlled way polycyclic aromatic compounds from isolable heteropine precursors. By way of example, the phenanthrene derivative 2 was obtained by heating the dibenzo[b,f]thiepine precursor 1 in the presence of copper

• absence of thermal solid-state reorganization [62]. This work thus unequivocally revealed the potential of thiepines and thiepine S-oxides as direct soluble precursors of polycyclic aromatic compounds with dual stimuli-responsiveness, thus opening the way to solution-based processing for the fabrication

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• for use in cutting-edge technologies. In particular, acenes, a subgroup of polycyclic aromatic compounds, are sought-after synthetic targets due to their remarkable optoelectronic properties which stem from their π-conjugation and planar structure. Despite all these promising characteristics, acenes

• ; biphenylene; [N]phenylenes; polycyclic aromatic compounds; Introduction Acenes represent an important category of carbon-rich polycyclic aromatic hydrocarbons (PAHs) characterized by the presence of linearly fused benzene rings [1][2]. Investigating the electronic properties of acenes is essential for

• review thus far have predominantly involved solution chemistry. However, recent reports have demonstrated the feasibility of producing biphenylene-containing polycyclic aromatic compounds through on-surface chemistry techniques. One of the initial examples was documented by Fasel and Meunier in 2017 [51

N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction

• Grigory Kantin,
• Pavel Golubev,
• Alexander Sapegin,
• Alexander Bunev and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136

• varying characteristics were selected as substrates for the studied insertion reaction, encompassing both aromatic and non-aromatic compounds differing in the number and arrangement of nitrogen atoms (Scheme 3). Notably, several of these heterocycles, including tetrahydroquinoline, 1,2,4-triazole, and

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• )aromatic compounds (Qx53) with a chalcogenodiazolo[3,4-b]pyrazine scaffold. These compounds exhibited narrow bandgaps (from 1.25 to 1.44 eV) and demonstrated n-type organic semiconductor properties [56]. Jin and co-workers focused on improving the charge-transfer characteristics of a semiconducting

First synthesis of acylated nitrocyclopropanes

• Kento Iwai,
• Rikiya Kamidate,
• Khimiya Wada,
• Haruyasu Asahara and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2023, 19, 892–900, doi:10.3762/bjoc.19.67

• example, when esters 1a are subjected to Lewis acid-induced denitration, highly electron-deficient enones (reaction b) [4] are obtained. The latter compounds are highly reactive and undergo reaction with, e.g., mercaptoacetaldehyde affording thiophenes (reaction c) [5] or with activated (hetero)aromatic

• compounds to give diarylated (oxoalkyl)malonates [6]. In the reaction using tin(II) chloride as the Lewis acid, the ring opening and nucleophilic attack of the nitro group occur, to produce functionalized isoxazolines (reaction d) [7]. In contrast, denitration under basic conditions generates highly

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

• Louis Monsigny,
• Floriane Doche and
• Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

• electron-withdrawing groups were functionalized and the expected products were isolated in moderate to high yields (4a–f, 58–91%). Palladium catalysis: Several works have been reported for the palladium-catalyzed trifluoromethylthiolation reaction of various aromatic compounds 5 by C–H bond activation and

• derivatives using AgSCF3 (Scheme 11) [124]. This methodology allowed the functionalization of several aromatic compounds bearing a pyridine or a pyrimidine as a directing group (20 examples, up to 65% yield). The reaction proceeded smoothly with substrates bearing an electron-donating group (25b,c), halogen

• from 5-methoxy-8-aminoquinoline, the functionalization of (hetero)aromatic compounds was achieved using 20 mol % of Pd(CH3CN)4Cl2 in the presence of TolSO2SeCF3 as the fluorinating source (14 examples, Scheme 17) [139]. Of note, when the reaction was carried out on derivatives bearing substituents at

Friedel–Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs)

• Swantje Lerch,
• Stefan Fritsch and
• Thomas Strassner

Beilstein J. Org. Chem. 2023, 19, 212–216, doi:10.3762/bjoc.19.20

• acylation; homogeneous catalysis; ionic liquids; iron catalysis; TAAILs; Introduction The Friedel–Crafts acylation is one of the oldest metal-catalyzed reactions in organic chemistry [1] and allows for the synthesis of a broad range of diverse compounds [2][3][4][5]. Starting from electron-rich aromatic

• compounds, acylation is possible by an organic acid chloride/acid anhydride and a Lewis acid [6][7]. In the course of the development of ionic liquids (ILs) as a reaction medium for chemical reactions [8][9], the Friedel–Crafts reaction was also examined [10][11][12][13][14][15][16]. First protocols were

Synthesis of meso-pyrrole-substituted corroles by condensation of 1,9-diformyldipyrromethanes with pyrrole

• Baris Temelli and
• Pinar Kapci

Beilstein J. Org. Chem. 2022, 18, 1403–1409, doi:10.3762/bjoc.18.145

• porphyrins, are tetrapyrrolic aromatic compounds, with the lack of one meso-carbon atom on the macrocycle [1][2][3][4]. This feature supplies a smaller ring cavity than in the case of porphyrins, three NH in the core, and coordination ability with high-valence transition metal ions. It is noteworthy that

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

• Dharmendra Das,
• Akhil A. Bhosle,
• Amrita Chatterjee and
• Mainak Banerjee

Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

• Representative examples of important halogen-containing aryl derivatives. Strategies for halogenation of aromatic compounds using NXS. General scheme of PEG-400-assisted halogenation of phenols and anilines in an automated grinder using NXS. Monohalogenation of phenols and anilines by automated grinding with NXS

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• annulene [12], and twisted naphthalene as central spacers [19]. As its close analogue, selenophene has properties very similar to those of thiophene. Fused aromatic compounds containing selenophene units show favorable optical and electrochemical properties and improved charge transport characteristics in

• the solid state mainly because such fused aromatic compounds often undergo increased Se–Se interactions, which confer ordering at the molecular scale and, thus, lead to well-aligned solid-state packing and excellent charge-transport properties [20][21]. However, as an important type of heteroacenes

• )2-bb-DSS), from which the TMS group could easily be removed by trifluoroacetic acid and replaced by bromine [27]. Another isomer of DSS, diseleno[3,2-b:2′,3′-d]selenophene (tt-DSS) has been successively synthesized from selenophene [28][29]. Among the limited fused aromatic compounds containing