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Search for "reaction mechanism" in Full Text gives 550 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

  • Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

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  • the reaction, the resulting deacylated compound 20 could be recovered in almost quantitative yield without any erosion of the enantiopurity. A possible reaction mechanism for this Pd-catalyzed three-component reaction was proposed (Scheme 3b). As shown, the reaction started with the oxidative addition
  • between β-ketoester 30 and di-tert-butyl azodicarboxylate (31), and the corresponding product 32 was obtained in 99% yield with 88% ee. A plausible reaction mechanism was proposed for this CPA-catalyzed enantioselective Groebke–Blackburn–Bienaymé reaction. As illustrated in Scheme 5b, the imine
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Published 19 Aug 2025

General method for the synthesis of enaminones via photocatalysis

  • Paula Pérez-Ramos,
  • Raquel G. Soengas and
  • Humberto Rodríguez-Solla

Beilstein J. Org. Chem. 2025, 21, 1535–1543, doi:10.3762/bjoc.21.116

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  • semipreparative scale for the reaction of 3-bromochromone (7a, 5.0 mmol) to afford enaminone 9a in a 68% isolated yield (Scheme 3). In terms of the reaction mechanism, TEMPO completely inhibited the reaction, implying the possibility of a radical intermediate in the reaction (Scheme 4A). Moreover, the TEMPO
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Letter
Published 29 Jul 2025

Photoredox-catalyzed arylation of isonitriles by diaryliodonium salts towards benzamides

  • Nadezhda M. Metalnikova,
  • Nikita S. Antonkin,
  • Tuan K. Nguyen,
  • Natalia S. Soldatova,
  • Alexander V. Nyuchev,
  • Mikhail A. Kinzhalov and
  • Pavel S. Postnikov

Beilstein J. Org. Chem. 2025, 21, 1480–1488, doi:10.3762/bjoc.21.110

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  • reactivity pattern in the current transformation, a reaction mechanism was proposed taking into the account the known data and control experiments (Scheme 4). Upon irradiation with blue light, the Ru(II) catalyst undergoes photoexcitation, followed by an oxidative single-electron transfer (SET) process with
  • using 1,2-dibromoethane as an internal standard. cNot detected by GC–MS. Proposed reaction mechanism. Optimization of the reaction conditions.a Supporting Information Supporting Information File 32: Experimental section, characterization data and control experiments. Acknowledgements Authors
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Published 21 Jul 2025

Wittig reaction of cyclobisbiphenylenecarbonyl

  • Taito Moribe,
  • Junichiro Hirano,
  • Hideaki Takano,
  • Hiroshi Shinokubo and
  • Norihito Fukui

Beilstein J. Org. Chem. 2025, 21, 1454–1461, doi:10.3762/bjoc.21.107

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  • absence of carbonyl groups in bis-olefin 5 has been corroborated by Fourier transform infrared (FTIR) spectroscopy (Figure S16 in Supporting Information File 1). Compound 4 could be generated through the reaction of compound 3 with phosphorus ylide. However, a reliable reaction mechanism remains unclear
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Letter
Published 14 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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  • full analysis can be obtained by also evaluating the activation volume (ΔV‡) data. Considering that all of the above studied reactions are multistep processes with several elementary steps, the determination of ΔV‡ requires a detailed theoretical reaction mechanism study that is beyond the scope of the
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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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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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  • demonstrated that both primary and secondary alcohols were compatible substrates (7a, 7f). The proposed reaction mechanism involves oxidative radical cyclization. Initially, TBHP undergoes homolytic cleavage to generate a tert-butoxy radical, which then forms an α-hydroxy carbon radical. This radical
  • -3-phenylpropanenitrile (16ha), were successfully employed to construct the target polycycles. To verify the reaction mechanism, a series of control experiments were conducted. The complete inhibition of the reaction by radical scavengers such as TEMPO, BHT, and hydroquinone suggested a radical
  • -mediated process. Based on the experimental results, a detailed reaction mechanism was proposed (Scheme 8). The reaction begins with the oxidative cleavage of an α-C(sp3)–H bond in acetonitrile (15) by the Sc(OTf)3/Ag2O system, generating an alkyl radical A through a single-electron-transfer (SET) process
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Published 24 Jun 2025

Synthesis of β-ketophosphonates through aerobic copper(II)-mediated phosphorylation of enol acetates

  • Alexander S. Budnikov,
  • Igor B. Krylov,
  • Fedor K. Monin,
  • Valentina M. Merkulova,
  • Alexey I. Ilovaisky,
  • Liu Yan,
  • Bing Yu and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2025, 21, 1192–1200, doi:10.3762/bjoc.21.96

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  • isolated in 77% yield (1.3 g, 4.61 mmol). In order to propose the reaction mechanism, control experiments were conducted (Scheme 4). The reaction is completely inhibited by the addition of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) or BHT (Scheme 4, reaction 1). A BHT-adduct derived from a P-centered
  • results and previous reports on copper(II) mediated oxyphosphorylation reactions [42][44][46][51][53], a plausible reaction mechanism is proposed (Scheme 5). The discovered transformation is unlikely to proceed via only a single route (see control experiments in Scheme 4), and the generation of phosphorus
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Published 20 Jun 2025

A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones

  • Ashutosh Nath,
  • John Mark Awad and
  • Wei Zhang

Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92

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  • (IMDA), and dehydrative re-aromatization reactions for the synthesis of imidazopyridine-fused isoquinolinones is developed. Gaussian computation analysis on the effect of the substitution groups for the IMDA reaction is performed to understand the reaction mechanism. Keywords: Groebke–Blackburn
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Published 13 Jun 2025

Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold

  • Henry S. T. Smith,
  • Ben Giuliani,
  • Kanchana Wijesekera,
  • Kah Yean Lum,
  • Sandra Duffy,
  • Aaron Lock,
  • Jonathan M. White,
  • Vicky M. Avery and
  • Rohan A. Davis

Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90

Graphical Abstract
  • -position (tele-substituted; Figure 1), distant from the halogen leaving group at position 5 [10]. A plausible reaction mechanism was proposed by Korsik et al. [10]. The antimalarial activity of series 4 triazolopyrazine scaffolds is generally reduced by substitution of an amine functionality at the 8
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Published 10 Jun 2025

Salen–scandium(III) complex-catalyzed asymmetric (3 + 2) annulation of aziridines and aldehydes

  • Linqiang Wang and
  • Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1087–1094, doi:10.3762/bjoc.21.86

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  • enantioselectivities and high diastereoselectivities. A reasonable reaction mechanism was proposed and rationalized the experimental results. Keywords: aldehyde; annulation; aziridine; oxazolidine; ring expansion; scandium triflate; Introduction Oxazolidine derivatives are an important class of nitrogen and oxygen
  • uses readily available components. On the basis of the experimental results and a previous report [16], a possible reaction mechanism is presented in Scheme 3. The catalyst (Cat) is first generated from salen L1 and Sc(OTf)3. Aziridines 1 coordinate to the Sc ion in the catalyst with their two
  • functionalized oxazolidine derivatives in moderate to good yields and good to excellent enantioselectivities and high diastereoselectivities. The stereocontrol was rationalized in the proposed reaction mechanism. Experimental Unless otherwise noted, all materials were purchased from commercial suppliers. Toluene
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Published 28 May 2025

Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C–N bond axial chirality

  • Natsume Akimoto,
  • Kaho Takaya,
  • Yoshio Kasashima,
  • Kohei Watanabe,
  • Yasushi Yoshida and
  • Takashi Mino

Beilstein J. Org. Chem. 2025, 21, 1018–1023, doi:10.3762/bjoc.21.83

Graphical Abstract
  • -catalyzed asymmetric allylic amination of allyl esters with isatin using (aR)-(−)-6 possesses an S-configuration. This stereochemical outcome follows the same reaction mechanism as the Pd-catalyzed asymmetric allylic substitution of allyl esters with indoles using (aR)-(−)-6 [31]. To explore further
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Published 23 May 2025

Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

  • Shyam Sathyamoorthi,
  • Appasaheb K. Nirpal,
  • Dnyaneshwar A. Gorve and
  • Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

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  • examples of amino-sulfonoxylations using tethered nitreniums. Putative reaction mechanism. (A) Scale-up and (B) applications. Optimization results. Structure–reactivity relationship with nitrenium tethers. Examination of sulfonic acid scope. Substrate scope exploration with an emphasis on stereocontrol and
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Published 19 May 2025

Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes

  • Patricia Gómez-Roibás,
  • Andrea Chaves-Pouso and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71

Graphical Abstract
  • not result in the formation of the dimerization product and complex mixtures of products were observed in these cases. To gather insight into the reaction mechanism, several control experiments were performed (Scheme 3). We first observed that the reaction does not take place in the absence of B2pin2
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Published 05 May 2025

Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers

  • Seeun Lim,
  • Teresa Kim and
  • Yunmi Lee

Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63

Graphical Abstract
  • 98% yield. Ortho-bromoaryl-substituted nitrile 3m also underwent tandem amidation and copper-catalyzed cyclization, efficiently producing lactam 9 in a 98% yield. Scheme 7 illustrates a plausible reaction mechanism based on previous studies [34]. The process begins with the formation of NHC–copper
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Published 17 Apr 2025

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

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  • -bidentate groups were unable to accelerate this reaction. To perform the reaction in an electrochemical environment, they used graphite (felt form) and nickel (nickel foam) electrodes as the anode and cathode, respectively, under a constant current of 8 mA at 110 °C. A non-radical reaction mechanism process
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Published 16 Apr 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

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  • ]. Based on this result, the implication of intermediate C in the reaction mechanism was demonstrated. However, an alternative pathway from intermediate A to the propargylamine product has been proposed when copper is used as the catalyst. In this case, the activation of the C–X bond of the dihaloalkane
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Published 13 Mar 2025

Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles

  • Constantine V. Milyutin,
  • Andrey N. Komogortsev and
  • Boris V. Lichitsky

Beilstein J. Org. Chem. 2025, 21, 556–563, doi:10.3762/bjoc.21.44

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  • conditions: 1c (1 mmol, 0.30 g), hydroxylamine hydrochloride (1.2 mmol, 0.08 g), EtOH (5 mL). Proposed reaction mechanism. Synthesis of product 13. Reaction conditions: 8o (1 mmol, 0.37 g), pivaloyl chloride (3 mmol, 0.36 g), MeCN (5 mL). Optimization of the reaction conditionsa. Supporting Information
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Published 13 Mar 2025

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

  • Yasushi Yoshida,
  • Maho Aono,
  • Takashi Mino and
  • Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

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  • present reaction, and products 17l and 17m were isolated in high yields with moderate to high stereoselectivities. The plausible reaction mechanism is shown in Figure 3. First, the removal of the acidic proton of the pre-nucleophile by potassium carbonate to form intermediate I, which undergoes cation
  • -amino cyanoesters with contiguous tetrasubstituted carbon stereogenic centers by the catalytic Mannich reaction. Further investigations into the reaction mechanism and product applications are ongoing in our group. Selected examples and applications of chiral halogen-bonding catalysts. Selected examples
  • for the construction of contiguous tetrasubstituted carbon centers via the Mannich reaction and this work. Plausible reaction mechanism. Catalyst screening for the asymmetric Mannich reaction. All yields were determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as an internal standard. N
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Published 12 Mar 2025

Electrochemical synthesis of cyclic biaryl λ3-bromanes from 2,2’-dibromobiphenyls

  • Andrejs Savkins and
  • Igors Sokolovs

Beilstein J. Org. Chem. 2025, 21, 451–457, doi:10.3762/bjoc.21.32

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  • improving the substrate scope and understanding the reaction mechanism are in progress in our laboratory. Synthesis of cyclic diarylbromonium compounds. Substrate scope. Reactions were performed on a 0.15 mmol scale. Yields were determined by 1H NMR spectroscopy of the reaction mixture using 1,2,3,4
  • : Representative jp vs v0.5 slope values for oxidation of Martin’s bromane precursor 6 (ref. [17]). D: Plausible reaction mechanism. Optimization of electrochemical oxidation/cyclization conditions.a Supporting Information Crystallographic data for the structure reported in this paper have been deposited with the
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Published 27 Feb 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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  • excess of quinone 3 leads to the formation of 2-(indolin-2-yl)-4,5,6,7-tetrachloro-1,3-tropolones 8a,b as final products. The detailed reaction mechanism in acetic acid solution was studied by the PBE0/6-311+G(d,p) method on the example of the interaction of 2-methylquinolines and 2-methylbenzazoles with
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Published 17 Feb 2025

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

  • Zi-Ying Xiao,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2025, 21, 286–295, doi:10.3762/bjoc.21.21

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  • has an E,E,E-configuration, while the compound 8a has a Z,E,E-configuration. On the basis of the above experiments and the previously published results [42][43][44][45][46][47][48][49][50][51][52], a plausible reaction mechanism was proposed in Scheme 4 to explain the formation of the various oxindole
  • ), CH3CN (5.0 mL), rt, 2 h; yields refer to isolated yields. Proposed reaction mechanism for the various compounds. Optimization of reaction conditions.a Dimerization of MBH carbonates of isatins.a Supporting Information The crystallographic data of compounds 5a (CCDC 2390713), 5j (CCDC 2390714), 6e (CCDC
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Published 06 Feb 2025

Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI

  • Zhenlei Zhang,
  • Ying Wang,
  • Xingxing Pan,
  • Manqi Zhang,
  • Wei Zhao,
  • Meng Li and
  • Hao Zhang

Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17

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  • 120 °C for 12 h; yield based on 3. Gram-scale synthesis of 2a and 4a and one-pot synthesis of 4a. Control experiments. Plausible reaction mechanism. Optimization of reaction conditions.a Supporting Information Supporting Information File 110: Experimental procedures, compound characterization data
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Published 03 Feb 2025

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

  • Yujun Pang,
  • Jinglan Yan,
  • Nawaf Al-Maharik,
  • Qian Zhang,
  • Zeguo Fang and
  • Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

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  • mixture, which significantly impeded the progress of the desired reaction. Therefore, on the basis of the above experimental results and previous reports [21][27][28][29][30], we proposed a possible reaction mechanism (Scheme 3b), taking CF2HCOOH as the illustrative example. Initially, a double ligand
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Published 30 Jan 2025

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

  • Seungmin Lee,
  • Minsuk Kim,
  • Hyewon Han and
  • Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

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  • theory (DFT) calculations, a proposed reaction mechanism is suggested as shown in Figure 3. Initially, copper acetylide INT-11 is formed by the reaction of acetylene with a copper precatalyst, leading to the formation of an N-acyl nitrene acetylide intermediate INT-12 after the incorporation of
  • late-stage functionalizations of complex scaffolds such as peptides, drug molecules, and natural products containing unprotected free OH and NH groups are anticipated. Proposed reaction pathway for the copper-catalyzed synthesis of δ-lactams from dioxazolones. Proposed reaction mechanism for the copper
  • -catalyzed synthesis of 1,2,4-triazole analogues from dioxazolones and N-iminoquinolinium ylides. Proposed reaction mechanism for the copper(I)-catalyzed synthesis of N-acyl amidines. Proposed reaction pathway for the copper-mediated synthesis of N-arylamides from dioxazolones. Proposed reaction pathway for
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Published 22 Jan 2025
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