Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

• Betty A. Kustiana,
• Galuh Widiyarti and
• Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

•  41B) [78]. Shankarling and co-workers (2020) directly prepared amide 12 from cinnamic acid (7) under solvent-free conditions catalyzed by graphene oxide via hydrogen-bonding activation (139) (Scheme 42A) [79]. The catalyst could be recycled multiple times without significant activity loss. Similarly

• ]. A similar reaction, reported by Zheng and co-workers (2020) utilized a graphene-supported Au/Pd catalyst to achieve the aerobic oxidative esterification of cinnamyl alcohol 157 via oxidation of the hemiacetal embedded in the catalyst surface 158 to obtain the corresponding ester 44 in quantitative

Carbon-rich materials: from polyaromatic molecules to fullerenes and other carbon allotropes

• Hiroko Yamada and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2025, 21, 798–799, doi:10.3762/bjoc.21.62

• ; polyaromatic molecules; In addition to diamond and graphite, traditional carbon allotropes in our old high-school textbook, new types of carbon allotropes, molecular carbons, were discovered in the last decades. These include fullerenes (1985) [1], carbon nanotubes (1991) [2], and graphene (2004) [3]. Due to

• became targets of Nobel Prizes in Chemistry (in 1996 to Carl, Kroto, and Smalley for the discovery of C60) and in Physics (in 2010 to Geim and Noboselov for the discovery of graphene). Prior to the celebration of the 40th anniversary of the discovery of fullerene in 2025, we planned this thematic issue

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

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

• definitively synthesized. The three-dimensional graphene-like carbons formed in a zeolite-template are the carbon forms that are the closest to carbon schwarzites so far [6][7]. Fragments of carbon schwarzites that retain their key structural characteristics are negatively curved polycyclic arenes [8][9

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

• Francesco Gambuti,
• Jacopo Pizzorno,
• Chiara Lambruschini,
• Renata Riva and
• Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

• -pot multistep synthesis of unprecedent 2,3-diaminoindolenines using graphene oxide (GO) as heterogeneous catalyst [21]. The protocol involves the three-component Ugi (3C-Ugi) reaction between aldehydes, isocyanides and 2 equivalents of electron-rich anilines to give α-aminoamidines, which undergo a C

• ] 3. Based on our experience on the use of graphene oxide (GO) as heterogeneous catalyst to promote MCRs and subsequent C–N bond oxidation [16][21], we first investigated the GO-promoted oxidation of N-Ph-THIQ and the subsequent 3C Ugi reaction to give α-aminoamidine 2a. Applying the previously

• without further purification. Graphene oxide (GO) was purchased from Graphenea. All products were characterized by 1H,13C, 19F (when fluorine is present) NMR, IR and HRMS. General procedure for the one-pot synthesis of spiro[indole-isoquinoline] 3a: A solution of N-phenyltetrahydroisoquinoline (1 equiv

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• summarized in a graphene map (Figure 5c). This shows that Cu-nanobrackets 1b preferentially recognize larger diameters with wider range (0.94–1.10 nm) than 1a (0.90–0.92 nm) due to the larger cavity with more flexibility of 1b than 1a. Theoretical calculations To interpret the diameter selectivity, the

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

• biased charges on the peripheral nitrogen atoms. Keywords: cross coupling; macrocycles; nitrogen doping; UV–vis spectroscopy; X-ray charge density analysis; Introduction Graphitic carbonaceous sheets of graphene continue to attract considerable attention, which lead us to explore structural defects

• ), 129.9 (CH), 127.5 (CH), 127.3 (CH); HRMS (APCI) (m/z): [M + H]+ calcd. for C44H29N4, 613.2387; found, 613.2366. Nitrogen-doped nanocarbons. (a) Schematic illustration of pyridinic nitrogen atoms installed at the interior and periphery of a graphene sheet. (b) Phenine nanocarbon molecules with nitrogen

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

• -magnetic guest molecule to activated carbon fibers (ACFs) as a nanographene-based host having localized spins originating from zigzag edges of graphene. The introduction of the guest molecule was confirmed by FTIR for ACFs-FeCp2 introduced at 55 (150) °C (FeCp2-ACFs-55(150)). The appearance of satellite

• interactions between the nanographene host and the guest molecules will be a promising strategy for developing a new class of molecular magnets. Keywords: charge transfer; ferrocene; graphene; host–guest; spin interaction; Introduction Nanocarbon host material, which is based on elements free from resource

• 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

Possible bi-stable structures of pyrenebutanoic acid-linked protein molecules adsorbed on graphene: theoretical study

• Yasuhiro Oishi,
• Motoharu Kitatani and
• Koichi Kusakabe

Beilstein J. Org. Chem. 2024, 20, 570–577, doi:10.3762/bjoc.20.49

• ) linkers on graphene. The activation barrier between two bi-stable conformations exhibited by PASE is confirmed to be based on the steric hindrance effect between a hydrogen on the pyrene group and a hydrogen on the alkyl group of this molecule. Even after the protein is supplemented, this steric hindrance

• graphene. We discuss the expected protein sensors when this type of energy surface appears and provide a guideline for improving the sensitivity, especially as an oscillator-type biosensor. Keywords: biosensor; DFT; PASE; protein; surface adsorption; Introduction Consideration of the atomic-scale motion

• of molecules based on nanoscience can lead to a better understanding of the behavior of target biomaterials and improve the sensitivity of specific dynamical systems, such as biosensors. In this study, we investigate the behavior of proteins immobilized with linker molecules on graphene substrates

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• nanocompounds, instead picking graphene oxide (GO), due to its unique morphology and high chemical stability (Scheme 20) [112]. The graphene oxide was decorated with CuBr nanoparticles, which had already shown great catalytic potential, forming the GO–CuBr complex that was utilized for the synthesis of BIMs

• graphene oxide would be expanded upon and enhanced by Masram and his research group a year later [113], who implemented La2O3 nanoparticles in place of the CuBr MNPs that Jain used, in solvent-free conditions. The La2O3/GO complex provided much faster reaction rates (25–60 min) and improved product

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

Electron-beam-promoted fullerene dimerization in nanotubes: insights from DFT computations

• Laura Abella,
• Gerard Novell-Leruth,
• Josep M. Ricart,
• Josep M. Poblet and
• Antonio Rodríguez-Fortea

Beilstein J. Org. Chem. 2024, 20, 92–100, doi:10.3762/bjoc.20.10

• molecules on surfaces like graphene or carbon nanotubes have allowed the scientific community to visualize at atomic resolution the structural changes of molecules in situ by single-molecule atomic-resolution real-time TEM imaging (SMART-TEM) [1][2][3][4][5]. Since the initial discovery [2], many movies

• similar systems with π–π interactions, as for example a “buckyball catcher” complex with C60 or the interlayer interaction between graphene sheets [16]. It is found to be significantly smaller than for C60@C240 [17], but larger than for C60@C540 and C60@C960 nanoonions [18]. The encapsulation energy of

Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

• Lorenzo Catti,
• Shinji Aoyama and
• Michito Yoshizawa

Beilstein J. Org. Chem. 2024, 20, 32–40, doi:10.3762/bjoc.20.5

• , and graphene nanoplatelets) are achieved through noncovalent encircling with the bent amphiphiles. The resultant imidazole-modified nanocarbons display a pH-responsive surface charge, as evidenced by NMR and zeta-potential measurements. In addition, solubilization of a nitrogen-doped nanocarbon (i.e

• of the side-chain present. Importantly, efficient water-solubilization and nonionic surface modification of nanocarbons (i.e., fullerene C60 (C60), single/multi-walled carbon nanotubes (s/m-CNT), and graphene nanoplatelets (GN)) can be achieved through noncovalent encircling with the present

Anion–π catalysis on carbon allotropes

• M. Ángeles Gutiérrez López,
• Mei-Ling Tan,
• Giacomo Renno,
• Augustina Jozeliūnaitė,
• J. Jonathan Nué-Martinez,
• Javier Lopez-Andarias,
• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2023, 19, 1881–1894, doi:10.3762/bjoc.19.140

• allotropes leads to SWCNTs and MWCNTs. Further expansion by unrolling nanotubes into infinite sheets leads to graphene 75 as formal homolog of SWCNTs 2 and graphite 76 as formal homolog of MWCNTs 3 (Figure 10) [112][114][115][116][117][118][119][120][121][122][123]. Graphite is the oldest, most common carbon

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• chiral nanographenes. Keywords: chiral nanographene; helicene; racemization barrier; Scholl reaction; single-crystal X-ray diffractometry; Introduction Graphene, an allotrope of carbon, has captured widespread attention since it was first experimentally demonstrated as a monolayer of carbon atoms [1

• ]. Graphene and graphene-based materials are consisted of sp2 carbons and have shown a variety of outstanding applications, particularly in electronic devices as conductor materials with a zero band gap [2][3]. Compared to infinite graphene, nanoscale graphene fragments exhibit size-dependent non-zero

• bandgaps, which significantly enhanced their semiconducting character [4][5]. Hence, the preparation of graphene segments, so-called nanographenes (NGs), has received much attention. In materials science, graphene fragments have been obtained by “cutting” graphene materials through specific chemical

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• singlet oxygen production have been identified in porphyrin-based butadiynes [7][8][9], 1,3-butadiyne-linked oligoporphycenes [10], and 1,3-butadiyne-linked amines [13]. A wide variety of applications was proposed for graphdiynes (2D allotropes of graphene), including electrocatalysts and energy devices

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• -doped graphene hybrid 96 through the CuAAC reaction. For the click reaction synthesis of hybrid 96, azide-functionalized N-doped graphene 94 and TMS-protected porphyrin 95 bearing an alkyne group were first prepared, as shown in Scheme 19. Subsequently, deprotected porphyrin bearing a terminal alkyne

• . The ultrafast pump-probe technique was used to determine the photoinduced charge separation in zinc porphyrin 96 and the rate constant was found on the order of 1010 s−1, clearly showing ultrafast electron-transfer between graphene and porphyrin units. Hence, these hybrids could be useful for light

• . The CuAAC click reaction has been shown to bind a variety of chromophores bearing azide or alkyne groups to the porphyrin periphery, including coumarin, xanthone, DNA, ferrocene, corrole, fluorescein, carborane, BODIPY, graphene, carboline, fullerene, NDI, β-cyclodextrin, cholic acid, quinolone, etc

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• cases, the formation of product 10 was observed with conversions of up to 90% [57]. In another approach, Uruş and co-workers used graphene oxide (GO)-supported bis(diphenylphosphinomethyl)amino GO@CHONHRN(CH2PPh2)2MX2 (M:Pd(II) and Pt(II))-type complexes as heterogeneous nanocatalysts, with Pd(II

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• ligand achieved the high activities of the Co-MS@MNPs/CS. Taking aryl halides and terminal alkynes as the reactants, Vajargahy and Dabiri discussed a facile method for a Sonogashira coupling reaction catalyzed by Pd/Co bimetallic nanoparticles supported on three-dimensional graphene (PdCoNPs-3DG) in

• aqueous medium under aerobic conditions (Scheme 26) [39]. The graphene support was prepared by oxidation of graphite, treatment of the resulting graphene oxide with ethylene diamine in an autoclave followed by freeze-drying to obtain three dimensional graphene with a high nitrogen content. Heating of the

• latter with salts of Pd(II) and Co(II) in ethylene glycol and water at pH 11 afforded the desired PdCo nanoparticles-3D graphene nanocomposite. The catalyst was then studied in the Sonogashira coupling reaction of arylacetylenes and aryl halides in the presence of various bases and solvents. The maximum

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• recognition of cholylglycine, which is a combination of cholic acid and glycine. The β-cyclodextrin/graphene oxide composite forms an inclusion complex with a β-NQS guest. The amino group of cholylglycine can bind to β-NQS by a nucleophilic substitution reaction, resulting in a decrease in the electrochemical

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• absorption, and novel electronic band structure, fills the gap between graphene and wide bandgap semiconductors [35][38]. Furthermore, BP shows a layer thickness tunable bandgap ranging between 0.3 and 2.1 eV. Therefore, BPNs can efficiently be applied as a photoredox catalyst with broadband solar absorption

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

• Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

• and Dockendorf prepared the corresponding 2,2’-sulfur-substituted compounds 90 by reacting tryptophan amines 89 and 90 with S2Cl2 under neutral and acidic conditions, respectively (Scheme 11b and Scheme 11c) [77][78]. Kamal took a different approach using a CuO nanoparticle-supported graphene-oxide

An initiator- and catalyst-free hydrogel coating process for 3D printed medical-grade poly(ε-caprolactone)

• Jochen Löblein,
• Thomas Lorson,
• Miriam Komma,
• Tobias Kielholz,
• Maike Windbergs,
• Paul D. Dalton and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2021, 17, 2095–2101, doi:10.3762/bjoc.17.136

• and many other substrates including ultra-nanocrystalline diamond, graphene and silicon carbide [22][23][24][25][26][27][28][29][30]. Even bottle-brush brushes could be prepared via SIPGP on various substrates for different applications [31][32][33]. Results and Discussion Here, we introduce SIPGP for