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Search for "complexes" in Full Text gives 1153 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications

  • Meng Qiu,
  • Jing Du,
  • Nai-Te Yao,
  • Xin-Yue Wang and
  • Han-Yuan Gong

Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106

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  • with Ru(II) to form NIR-emissive complexes that exhibit redox-responsive chiroptical switching, notably with complex 8 showing reversible electronic circular dichroism (ECD) upon oxidation [21]. Liao and co-workers introduced a narrowband CP-TADF emitter 9, characterized by a narrow emission bandwidth
  • −1 (Table 3). Importantly, both dimers displayed selective fluoride ion recognition through hydrogen bonding, with (M,M)-12c exhibiting a high binding constant (Ka = 2 × 105 M−1). The resulting [12c·F−] and [12d·F−] complexes exhibited red-shifted circular dichroism (CD), fluorescence, and CPL
  • , the team achieved the enantioselective synthesis of heterodehydrospiroenes on a gram scale using chiral vanadium(V) complexes – marking a significant advancement in asymmetric electrochemical catalysis. In a complementary study that same year, they reported a two-step electrochemical synthesis of a
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Published 11 Jul 2025

High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters

  • Kelsey Plasse,
  • Valerie Wright,
  • Guoshu Xie,
  • R. Bernadett Vlocskó,
  • Alexander Lazarev and
  • Béla Török

Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102

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  • imidazole-based N-heterocyclic carbene (NHC)–CuCl complexes [40]. However, their synthesis is often tainted by the use of toxic reagents and solvents. In addition, when o-phenylenediamine reacts with ketones, the common catalytic methods yield benzodiazepine products [41]. In our case the reaction of o
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Published 02 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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  • reduction of the Ni(II) pre-catalyst) via oxidative addition, radical coupling and reductive elimination. The last step is a single-electron transfer between the resulting Ir(II) and Ni(I) complexes, regenerating the active catalysts and closing the two cycles. In 2021, Romanov-Michailidis and Knowles et al
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Published 27 Jun 2025

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

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  • methods utilizing electron donor–acceptor (EDA) complexes and peroxide initiators have recently gained attention due to their operational simplicity and environmental friendliness. In 2024, Song’s group and co-workers presented a novel metal-free, visible-light-promoted method for synthesizing
  • difluoroamidated oxindoles via electron donor–acceptor (EDA) complexes (Scheme 37) [23]. The method involved the use of N-phenylacrylamides and bromodifluoroacetamides as starting materials, with N,N,N’,N’-tetramethylethylenediamine (TMEDA) acting as the electron donor. The reaction proceeded efficiently under
  • energy (327 kJ/mol) and is less reactive compared to alkyl bromides or iodides. Previous methodologies predominantly relied on alkyl bromides and iodides due to their lower bond dissociation energies. By leveraging the excited-state reactivity of Pd(0) complexes under blue LED irradiation, this method
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Published 24 Jun 2025

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

  • Julius Seumer,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

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  • activation, transforming these inert bonds into reactive carbon–transition metal (C–M) bonds. Subsequent transformations of these complexes enable the formation of an array of new functional groups, such as carbon–carbon and carbon–heteroatom bonds, underpinning a plethora of synthetic applications
  • literature sample from Chen and colleagues [4]. 2. Next, we identify all relevant palladacycle complexes involved in the C–H activation facilitated by ortho-directing groups. For each match, a model complex is constructed containing the substrate and a Pd atom. In this complex, the Pd atom is bonded to the
  • carbon at the reaction site and to the heteroatom of the directing group, as illustrated in Figure 5. To assess the geometry of these complexes, we generate a 2D structure using RDKit, where all atoms are constrained to lie in a single plane. Although this type of 2D embedding is typically used only for
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Published 16 Jun 2025

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

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  • organic compounds, with the driving forces leading to inclusion being van der Waals and hydrophobic interactions for apolar guests, and/or hydrogen bonding when the guest features H-bond accepting groups that interact with the hydroxy groups of the cyclodextrins. Interactions with metal ions/complexes and
  • coordination with inorganic and organometallic complexes involves hydrophobic interactions and van der Waals forces (mainly with the organic parts of these guests). Several forces are at play in the formation of supramolecular assemblies with gold in the form of haloaurate ions, as detailed in the forthcoming
  • networks to optimize the chemical parameters of the extraction. An optimal value of gold removal, lying between 98 and 98.9%, was found to occur with a contact time of 40 minutes, a concentration of α-CD of 11.61 g/L and KOH was added in enough quantity to raise the solution pH to 5 [47][48]. Complexes of
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Published 06 Jun 2025

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

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  • and I. Without any metal coordination, DFT suggests conformer I is more stable than conformer II by ≈60 kJ/mol. However, upon complexation with Li+, both complexes 2 and 3 are remarkably similar in energy with the difference of less than 1 kJ/mol. This very small energy difference should be too small
  • for marked differences in the arrangement of groups in space. The overlaid image of lithium complexes 2 and 3 (Figure 8) shows the similar arrangement of all groups on plane except for one benzyl ring (highlighted by a red asterisk) in complex 2 that faces outside the interior of the macrocycle. A
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Published 30 May 2025

Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

  • Valentina Benazzi,
  • Arianna Bini,
  • Ilaria Bertuol,
  • Mariangela Novello,
  • Federica Baldi,
  • Matteo Hoch,
  • Alvise Perosa and
  • Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

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  • + species, a process where transition-metal-based complexes are employed [29], often (in the case of Ru(II)-based derivatives) in the presence of tertiary amines as sacrificial reductants [27][28]. Nonetheless, while this work serves primarily as a preliminary study comparing the reducing power of various
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Published 26 May 2025

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

  • Daniel Straub,
  • Markus Gross,
  • Mona E. Arnold,
  • Julia Zolg and
  • Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

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Published 21 May 2025

Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts

  • Katy Medrano-Uribe,
  • Jorge Humbrías-Martín and
  • Luca Dell’Amico

Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76

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  • powerful tool for the construction and functionalization of organic molecules and materials. Thus, the scientific community has focused on the design and study of new organic molecules that can be used as photocatalysts, replacing generally more expensive metal-based complexes [1][2][3]. Furthermore, there
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Published 14 May 2025

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

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  • utilizing in situ-generated π-allylpalladium complexes to capture strained cyclic allene intermediates (Scheme 4) [22]. By modulating the ligands in the reaction system, two distinct polycyclic scaffolds, 13 or 14, could be synthesized with high selectivity. Mechanistically, the Pd(0) catalyst coordinates
  • annulations of strained cyclic allenes with π-allyl palladium complexes and proposed mechanism [22]. Ring expansion of benzosilacyclobutenes with alkynes [23]. Photoinduced regiodivergent and enantioselective cross-coupling [24]. Catalyst-controlled regiodivergent and enantioselective formal hydroamination of
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Published 07 May 2025

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

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  • interactions between K+ and C=O moieties [31], similar to these seen in the single crystal structures of KF and K2CO3 complexes. These provide a promising opportunity that can be used to identify the cooperative interaction underpinning complexed ions in dual-host strategy-based extraction. To do this, the
  • − was 4:5:4:2 in the crystalized structure. Like the structure of K2SO4 complexes [31], one Cs+ cation is encapsulated by 18-crown-6 and further stabilized by one ion-dipole interaction with the O=C unit of the hexaurea receptor. The Cs···O distance is measured at 3.2 Å. The other two Cs+ cations are
  • by 1H NMR titrations in DMSO. The resulting complexes after solid–liquid extraction were also characterized by 1H NMR spectroscopy (Figure 3), showing consistent anion binding profiles. By comparing with free hexaurea receptor L, the chemical shifts of the urea units N–H in the obtained complexes are
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Published 29 Apr 2025

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

  • Xuhong Zhao,
  • Weishuang Li,
  • Mengli Yang,
  • Bojie Li,
  • Yaoyao Zhang,
  • Lizhen Huang and
  • Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

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  • ]. Furthermore, dicopper(I) complexes can also be used as an effective catalyst in Ullmann-type N-arylation/cyclization of 2-bromobenzoic acids with amidines, providing the corresponding quinazolinones in good yields [15]. Despite the high efficiency of the above-mentioned copper catalysts in the synthesis of
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Published 28 Apr 2025

4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

  • Nguyen Tran Nguyen,
  • Vo Viet Dai,
  • Luc Van Meervelt,
  • Do Thi Thao and
  • Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

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  • interactions also contribute to the stabilization of the ligand–iNOS complexes. In particular, 4-(1-methylamino)ethylidene-5-phenyl-1-(3-nitrophenyl)pyrrolidine-2,3-dione (5e) exhibited the strongest binding affinity (−9.51 kcal/mol) and demonstrated significant inhibitory activity against nitric oxide (NO
  • π–π stacking is observed in the crystal packing of the complexes, but only C–H···π interactions are present. Two C–H···O hydrogen bonds complete the interactions stabilizing the crystal packing (Figure S1 and Table S2 in Supporting Information File 1). Inhibitory activity of NO production It is
  • , Trp194, Gly202, Pro350, Phe369, and Tyr489, further contributing to the stabilization of the ligand–protein complexes. More importantly, the occurrence of an electron-withdrawing group, nitro group (NO2), on the aromatic ring linked to the 1-position of the pyrrolidine-2,3-dione core may help compound 5e
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Published 24 Apr 2025

Development and mechanistic studies of calcium–BINOL phosphate-catalyzed hydrocyanation of hydrazones

  • Carola Tortora,
  • Christian A. Fischer,
  • Sascha Kohlbauer,
  • Alexandru Zamfir,
  • Gerd M. Ballmann,
  • Jürgen Pahl,
  • Sjoerd Harder and
  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2025, 21, 755–765, doi:10.3762/bjoc.21.59

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  • applications of calcium complexes with axially chiral BINOL phosphate ligands have been reported in recent years [28][32][33][34][35][36][37][38], as well as complexes with other chiral phosphoric acid ligands [39]. Since then, other main group metal complexes with BINOL phosphate ligands have been discovered
  • ]. As observed earlier [53], cis/trans preferences in octahedral calcium complexes are influenced by small changes in sterics. Further details on the structure of 4 can be found in Supporting Information File 1. Complex 4 appeared to be a well-defined achiral model system for the catalyst combination
  • , resulting in detachment of the cyanide carbon from the calcium atom to yield an isocyanide complex 9 [55], in which the preferred side of attack on the imine carbon of the hydrazone is already predetermined (i.e., from either Re or Si face). Notably, in both complexes formed from E- and Z-hydrazone, an
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Published 14 Apr 2025

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

  • Leon M. Friedrich and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

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  • simulation (MD) [54] over 10 ns to determine the relative stability of the complexes (Supporting Information File 1, Figure S17 and Figure S18). The most stable receptor–ligand complexes so obtained were then submitted to a MM-GBSA calculation to deliver IFD binding energies (Table 3 and Supporting
  • Information File 1, Table S25). Also the binding energies obtained with IFD for 6αMan 4 and 3αMan 5 are in accordance with the experimental data as they predict correctly that the ligand–FimH complexes formed with the E isomers of 4 and 5 are more stable than the complexes formed with the respective Z isomers
  • . These differences correspond to the structures of the various ligand–FimH complexes (Figure 4A and B), however, it is difficult to substantiate the measured binding differences in detail. For example, it is not apparent that secondary interactions performed by the scaffold mannoside portion in the
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Published 08 Apr 2025

Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA

  • Raphael Bereiter and
  • Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56

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  • with an electrophilic handle for the covalent attachment of the surrogate to the RNA. The resulting irreversibly tethered dye–RNA complexes have opened up new avenues for RNA imaging in live cells. Here, we report the syntheses of such modified HBC530 ((4-((2-hydroxyethyl)(methyl)amino)benzylidene
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Published 04 Apr 2025

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

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  • ][22][23][24][25][26]. Within these families of macrocyclic hosts, CB[n] molecular containers have proven particularly versatile because they form high affinity CB[n]–guest complexes in aqueous solution that are responsive to various stimuli (e.g., photochemical, electrochemical, chemical) [27][28][29
  • sidewalls and the ureidyl π-systems. The small changes in chemical shift for the methonium group suggests it is located near the ureidyl C=O portals and not inside the magnetically shielding cavity. Related complexation-induced changes in chemical shift are observed for the other C1·guest complexes (Figure
  •  4b), we observe separate resonances for free Me6PXDA and complexed C1·Me6PXDA which means that the rate of guest exchange is slow on the chemical shift timescale. Slow kinetics of guest exchange is commonly observed for tight host·guest complexes. In contrast, the kinetics of guest exchange are in
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Published 03 Apr 2025

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

  • Maurizio Iannuzzi,
  • Thomas Hohmann,
  • Michael Dyrks,
  • Kilian Haoues,
  • Katarzyna Salamon-Krokosz and
  • Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52

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  • pathways are heavily time-consuming and synthetically challenging. In this context, chiral Ni(II) complexes can be powerful tools to obtain tailor‑made non‑canonical amino acids. In this work, we wanted to take advantage of this strategy and extend the range of this method to include additional fluorinated
  • diastereomerically pure γ‑branched fluorinated amino acids. This work further underlines the importance of chiral Ni(II) complexes in the synthesis of fluorinated amino acids. Keywords: chiral nickel complexes; fluorinated amino acids; gram-scale amino acid synthesis; stereoselective synthesis; Introduction Non
  • chiral nickel complexes. In recent years, the Soloshonok working group demonstrated the synthesis of non‑natural amino acids using the corresponding chiral Ni(II) complex [7]. In addition to the high enantiomeric purity of the corresponding products, the scale of the reaction, which extends into the
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Published 21 Mar 2025

Recent advances in allylation of chiral secondary alkylcopper species

  • Minjae Kim,
  • Gwanggyun Kim,
  • Doyoon Kim,
  • Jun Hee Lee and
  • Seung Hwan Cho

Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51

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  • electronegativity, reaching 1.648 Å in the reactive alkoxytrialkyl complex D and 1.659 Å in the tetraalkyl "ate" complex E. The B–C bond lengths in amido- and alkyl-substituted boronic ester complexes B and C fell between these extremes, suggesting an intermediate level of activation. These findings prompted
  • including s-BuLi, n-BuLi, and PhLi. The optimized protocol, employing CuCN as a catalyst, enabled efficient coupling between t-BuLi-activated complexes 10 and allylic halides 11, furnishing products 12 with complete retention of stereochemistry and high yields (Scheme 7). The method's versatility and
  • boronate complexes and correlation with reactivity. Copper-catalyzed stereospecific allylic alkylation of secondary alkylboronic esters via tert-butyllithium activation. Copper-catalyzed stereospecific allylic alkylation of chiral tertiary alkylboronic esters via adamantyllithium activation. DFT-calculated
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Published 20 Mar 2025

Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether

  • Gianpaolo Gallo and
  • Bartosz Lewandowski

Beilstein J. Org. Chem. 2025, 21, 541–546, doi:10.3762/bjoc.21.42

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  • H-ʟ-Trp-OH is also considerably higher than the values observed for the complexes of previously reported crown ether-type receptors with zwitterionic amino acids in water [22]. The affinity of 1 towards leucine, bearing a hydrophobic side chain, is over 4 times lower than towards tryptophan (entry 2
  • tryptophan and Trp-containing peptides by 1 we performed NMR measurements on the 1:1 host–guest complexes in D2O. Upon binding of tryptophan by 1 a significant upfield shift of the aromatic protons and a slightly smaller shift, also upfield, of the α and β-Trp protons was observed (Figure 3). The aromatic
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Published 10 Mar 2025

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

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  • used to achieve higher yields [27]. Even in the absence of a transition-metal-based photosensitizer, a recent study showed that perfluoroalkylation using perfluoroalkyl iodides (RFI) could be carried out by activation of the RF–I bonds by formation of electron donor–electron acceptor complexes with an
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Published 07 Mar 2025

Synthesis of electrophile-tethered preQ1 analogs for covalent attachment to preQ1 RNA

  • Laurin Flemmich and
  • Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

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  • an electrophilic handle for the covalent attachment of the ligand to the RNA. The simplicity of the underlying design of irreversibly bound ligand–RNA complexes has provided a new impetus in the fields of covalent RNA labeling and RNA drugging. Here, we present short and robust synthetic routes for
  • , DPQ1) and haloalkyl-modified preQ1 and DPQ1. B) The ligand classes of XcnpreQ1 and XcnDPQ1 allow specific formation of covalent small molecule–RNA complexes as has been recently demonstrated (see ref. [4]). Electrophile (E). Three-step syntheses of preQ1 (1) and DPQ1 (2). For the synthesis of m6preQ1
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Published 04 Mar 2025

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

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  • observed in dilute solutions because of the formation of aggregates perturbing electronic transitions [51][52][53]. Moreover, at high concentrations, the formation of electron donor–acceptor (EDA) complexes [54] or exciplexes is expected to be favored, and the effect of mechanical forces on these is worth
  • zinc cations to align 1.1 through the formation of hydrogen-bonded coordination complexes. Thus, when a single crystal of the [Zn(bpe)2(H2O)4](NO3)2·8/3H2O·2/3bpe complex was exposed to UV irradiation (dark blue phosphor lamps, λ = 350 nm) for 25 h, only 46% conversion to 1.2 was observed via 1H NMR
  • instead of 2 h in a row) proved beneficial to minimize heat accumulation resulting in product decomposition. Next, the authors proved the generality of mechanoluminescence by performing the sulfonylation of alkenes via EDA-complexes photochemistry (Scheme 12B). Thus, when a mixture of 1,1-diphenylethylene
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Perspective
Published 03 Mar 2025

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

  • Yurii A. Sayapin,
  • Eugeny A. Gusakov,
  • Inna O. Tupaeva,
  • Alexander D. Dubonosov,
  • Igor V. Dorogan,
  • Valery V. Tkachev,
  • Anna S. Goncharova,
  • Gennady V. Shilov,
  • Natalia S. Kuznetsova,
  • Svetlana Y. Filippova,
  • Tatyana A. Krasnikova,
  • Yanis A. Boumber,
  • Alexey Y. Maksimov,
  • Sergey M. Aldoshin and
  • Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

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  • sensitivity of in situ obtained complexes 9 and 10 with CN− to different cations. It appeared that the addition of an equivalent amount of Hg(ClO4)2 to an acetonitrile solution selectively and completely restores the initial absorption and fluorescence spectra (Scheme 3). Thus, the obtained compounds
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Published 17 Feb 2025
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