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Search for "scale up" in Full Text gives 193 result(s) in Beilstein Journal of Organic Chemistry.

Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

  • Youlong Du,
  • Haibo Mei,
  • Ata Makarem,
  • Ramin Javahershenas,
  • Vadim A. Soloshonok and
  • Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

Graphical Abstract
  • catalytic cycle. Finally, the acetimidic anhydride D undergoes a Mumm rearrangement to furnish the desired β-trifluoromethyl diacylamino ester 4a. The final goal of this work is the examination of the scale-up applicability of this three-component tandem reaction (Scheme 5). To our delight, the reaction
  • . Control experiments. Proposed reaction mechanism. Scale-up synthesis. Optimization of reaction conditions.a Supporting Information Supporting Information File 8: Experimental details and spectral data. Funding We gratefully acknowledge the financial support from the National Natural Science Foundation
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Published 02 Feb 2024

Optimizing reaction conditions for the light-driven hydrogen evolution in a loop photoreactor

  • Pengcheng Li,
  • Daniel Kowalczyk,
  • Johannes Liessem,
  • Mohamed M. Elnagar,
  • Dariusz Mitoraj,
  • Radim Beranek and
  • Dirk Ziegenbalg

Beilstein J. Org. Chem. 2024, 20, 74–91, doi:10.3762/bjoc.20.9

Graphical Abstract
  • due to extended ion transport distances. These effects cause significant potential losses, eventually reducing the efficiency of the reactors. The addition of large amounts of supporting electrolyte and vigorous circulation of the electrolyte solution also complicates the scale-up process [17][18]. On
  • the contrary, expanding photocatalytic systems, particularly those employing powdered photocatalysts, to a larger scale is notably more straightforward [17][18]. However, complications arise when attempting to scale up reactors solely based on geometric similarity, as alterations in mixing and
  • hydrodynamic attributes occur during the process of scale-up [19][20]. Therefore, a suitable reactor, which ensures excellent fluid dynamics and transport properties during scale-up, is needed for photocatalytic hydrogen generation. Loop reactors utilize partial inner circulation of the chosen reaction medium
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Published 16 Jan 2024

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

  • Bel Youssouf G. Mountessou,
  • Élodie Gisèle M. Anoumedem,
  • Blondelle M. Kemkuignou,
  • Yasmina Marin-Felix,
  • Frank Surup,
  • Marc Stadler and
  • Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

Graphical Abstract
  • ) profile, was scale up fermented to give 12 g of culture extract. This extract was subjected to a silica gel column chromatography to give several fractions, which were further purified over normal and reversed-phase HPLC to yield 2-ethyl-2,6-dihydroxy-5,7-dimethylbenzofuran-3-one (1), 3,9
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Published 13 Oct 2023

Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

  • Tzu-Yu Huang,
  • Mario Djugovski,
  • Sweta Adhikari,
  • Destinee L. Manning and
  • Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

Graphical Abstract
  • azido amine intermediate INT-3 can be formed via vinylic substitution of INT-1 with an azide which can cyclize to form INT-4 that subsequently aromatizes to afford product 3 (route B). To demonstrate the applicability of this method, a scale-up reaction was performed using 150 mg of the limiting reagent
  • , which is five times the usual reaction scale used in substrate scope screening or optimization experiments (Figure 6). In this scale-up experiment, we obtained the product with 57% yield , which is slightly lower than 70% using 1-(2,2-difluorovinyl)-4-methylbenzene (1, 154 mg, 1 mmol, 1 equiv), 4
  • . Proposed mechanism. Scale-up experiment. Optimization of reaction conditions.a Supporting Information Supporting Information File 2: General information, experimental procedures for all the substrates and intermediates, characterization data, and NMR spectra (1H, 19F, and 13C NMR). Funding Research
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Published 05 Oct 2023

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

  • Damiano Diprima,
  • Hannes Gemoets,
  • Stefano Bonciolini and
  • Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

Graphical Abstract
  • protocol demonstrates excellent scalability, as we have successfully transferred it to the HANU flow reactor. This flow photoreactor is designed for multi-phase reactions (solid–liquid, gas–liquid) [30][31][32], and allows for seamless scale-up to production scale. Finally, by the use of specific “easy to
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Published 31 Jul 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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Published 28 Jul 2023

Light-responsive rotaxane-based materials: inducing motion in the solid state

  • Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

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  • light-responsive intertwined materials and the industrial scale-up production usually hindered by the low yield of the interlocked molecules. Thus, future research efforts should be focused on the development of novel synthetic methodologies to access to such interlocked architecture, as well as the use
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Published 14 Jun 2023

Honeycomb reactor: a promising device for streamlining aerobic oxidation under continuous-flow conditions

  • Masahiro Hosoya,
  • Yusuke Saito and
  • Yousuke Horiuchi

Beilstein J. Org. Chem. 2023, 19, 752–763, doi:10.3762/bjoc.19.55

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  • high mixing efficiency throughout the reaction. This complex equipment complicates its versatile application for the scale-up and manufacturing, which leads to higher costs. To address this issue, we turned our attention to the use of porous material, which is widely used for exhaust gas treatment in
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Published 31 May 2023

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

  • Péter Kisszékelyi and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

Graphical Abstract
  • structurally different Michael acceptors were successfully applied. Their work also included a 3 mmol scale-up (62%, 87% ee, dr >20:1) and various derivatizations of the Mannich products. Furthermore, they have also attempted a multi-electrophile cascade reaction, which harnesses the nucleophilic nature of the
  • thoroughly examined using DFT calculations. Other than the broad substrate scope, the synthetic utility of this method was demonstrated by a scale-up reaction (3.73 mmol scale, 87% yield, 88% ee), and by several different transformations of the tandem products. Similarly, Ghorai et al. studied a Cu-catalyzed
  • cascade borylation/Michael addition sequence leading to enantioenriched spiroindane boronates 174 (Scheme 44A) [85]. The reaction showed good functional group tolerance. Further derivatization, as well as scale-up (1 mmol) of the reaction were successfully performed (72% yield, 89% ee, dr >20:1). Based on
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Published 04 May 2023

C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

  • Grédy Kiala Kinkutu,
  • Catherine Louis,
  • Myriam Roy,
  • Juliette Blanchard and
  • Julie Oble

Beilstein J. Org. Chem. 2023, 19, 582–592, doi:10.3762/bjoc.19.43

Graphical Abstract
  • processes rely on the use of a homogeneous metal catalyst at elevated temperatures necessary to cleave the C3–H bond by oxidative addition. These experimental conditions, easily used in the laboratory, are potentially problematic for scale-up due to efficiency and safety issues (related to the high
  • , not only a unique control of reaction parameters, such as improved mass and heat transfer, but also reduced safety risks and increased reproducibility of the results [29][35][36]. These features should therefore allow us to scale up our directed C3-functionalizations of furfurylimines under safe
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Published 03 May 2023

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

  • Alena V. Dmitrieva,
  • Oleg A. Levitskiy,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

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  • stereoselectivity level. Additionally, Schiff base derivatives of L7 have a considerably higher solubility in acetonitrile as compared to the L4-based complexes (see Table 3 and Supporting Information File 1); this makes it easier to scale-up the synthesis (e.g., for the SN2 alkylations or nucleophilic addition
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Published 27 Apr 2023

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

  • Eric Gayon,
  • Guillaume Lefèvre,
  • Olivier Guerret,
  • Adrien Tintar and
  • Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

Graphical Abstract
  • halides was observed and the cross-coupling products were afforded in good to excellent yields (Scheme 5). Moreover, this reaction can also be carried out at the gram scale (up to 50 mmol for alkyl–alkenyl coupling reactions, up to 10 mmol for alkyl–aryl couplings). Alkoxide salts, such as EtOMgCl, are
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Published 14 Feb 2023

Synthetic study toward tridachiapyrone B

  • Morgan Cormier,
  • Florian Hernvann and
  • Michaël De Paolis

Beilstein J. Org. Chem. 2022, 18, 1741–1748, doi:10.3762/bjoc.18.183

Graphical Abstract
  • yield but the scale-up of the reaction was less efficient [33]. It has to be underlined that all attempts, using either methods, to couple aldehyde 9 with 2-methylpent-1-en-3-one and directly produce 13 were unsuccessful. To achieve this goal a methylation step of 12 (LiN(iPr)2 (LDA); MeI) was thus
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Published 19 Dec 2022

Inline purification in continuous flow synthesis – opportunities and challenges

  • Jorge García-Lacuna and
  • Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

Graphical Abstract
  • chemistry tools developed in academia. Keywords: flow synthesis; inline purification; process development; reaction telescoping; scale-up; Introduction Continuous flow chemistry is a mature and widely applied platform technology that exploits intrinsic advantages over batch processing such as better heat
  • system for purifying mixtures in a continuous fashion by using alternating sample loops and chromatography columns (Scheme 1). This system thus acts as a scale-up preparative HPLC. Two different sample loops are loaded with the crude reaction mixture, and therefore, the crude material is injected into
  • of alcohols using a phase transfer catalyst (PTC) [55]. In a scale-up run, a three-stage counter-current cascade was used downstream of the first separation to remove the PTC (Scheme 4). In this scenario more than 90% of the phase transfer catalyst was separated from the phase containing the desired
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Published 16 Dec 2022

An alternative C–P cross-coupling route for the synthesis of novel V-shaped aryldiphosphonic acids

  • Stephen J. I. Shearan,
  • Enrico Andreoli and
  • Marco Taddei

Beilstein J. Org. Chem. 2022, 18, 1518–1523, doi:10.3762/bjoc.18.160

Graphical Abstract
  • of us, was limited to 0.543 g (1 mmol) of substrate. Scale up of this protocol was not attempted, but it might become problematic due to issues with microwave penetration in a medium that contains a strong absorber, such as the Ni catalytic complex. In this work, we have employed either 5.0 g (15.3
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Published 07 Nov 2022

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

  • Shang-Feng Yang,
  • Pei Li,
  • Zi-Lin Fang,
  • Sen Liang,
  • Hong-Yu Tian,
  • Bao-Guo Sun,
  • Kun Xu and
  • Cheng-Chu Zeng

Beilstein J. Org. Chem. 2022, 18, 1249–1255, doi:10.3762/bjoc.18.130

Graphical Abstract
  • . To demonstrate the practicability of the reaction, a scale-up reaction of ethyl acetoacetate (1a, 28 mmol, 3.64 g) and thiourea (2a,14 mmol, 1.05 g) was carried out under the optimized conditions to give 3a in 50% yield (Scheme 3). In order to better understand the iodide-mediated reaction mechanism
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Published 15 Sep 2022

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

  • Mana Kitano,
  • Tsuyoshi Saitoh,
  • Shigeru Nishiyama,
  • Yasuaki Einaga and
  • Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

Graphical Abstract
  • , where the BDD’s wide potential window enables the direct anodic oxidation of cumene into the cumyl cation. Since electricity is directly employed as the oxidizing and reducing reagents, the present protocol is easy to use, suitable for scale-up, and inherently safe. Keywords: aromatic alkyl; boron
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Published 07 Sep 2022

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

  • Kouichi Matsumoto,
  • Yuta Hayashi,
  • Kengo Hamasaki,
  • Mizuki Matsuse,
  • Hiyono Suzuki,
  • Keiji Nishiwaki and
  • Norihito Kawashita

Beilstein J. Org. Chem. 2022, 18, 1116–1122, doi:10.3762/bjoc.18.114

Graphical Abstract
  • -chloroacetates in Bu4NBr/DMF using a divided cell equipped with Pt electrodes to produce the corresponding cyclopropane derivatives in moderate yields were discovered. The reaction conditions were optimized, the scope and limitations, as well as scale-up reactions were investigated. The presented method for the
  • -chloroacetates to cyclopropane derivatives has been developed. The reaction has been optimized, the scope and limitations have been investigated. Scale-up reactions were performed and satisfactory yields obtained. The generation of an EGB of the enolate ion from alkyl 2-chloroacetates is indicated. The current
  • cyclopropanetricarboxylates. Previous reports (reactions 1–3) and this work (reaction 4). Plausible reaction mechanism. EGB = electrogenerated base. Reaction optimization. Effect of electricity around 1 F/mol and type of electrochemical cell. Scope and limitations. Scale-up experiments. Supporting Information Supporting
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Published 29 Aug 2022

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

Graphical Abstract
  • ortho- and para-positions. The gram-scale reaction shows similar efficiency like smaller batches indicating easy scale-up of this protocol. The method is environmentally friendly and cost-effective having key attributes like simple instrumentation, no aqueous workup, short reaction time, and mild
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Published 09 Aug 2022

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

  • Daniele Rocco,
  • Ana A. Folgueiras-Amador,
  • Richard C. D. Brown and
  • Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

Graphical Abstract
  • technique. Again, productivity for the esterification is four-fold higher (3.65 mmol/h, 0.1 M solution) in flow than in batch (0.97 mmol/h, pure IL), and in flow the reaction volume could simply be increased to allow scale-up, obviously in a longer time. Conclusion The results reported in this work
  • scale up. In the case of the flow procedure, a 0.1 M solution of the IL is employed, which may be more convenient than using pure ILs. Further investigations of electrogeneration of NHCs and applications in organic synthesis are underway. Experimental Materials and methods Chemicals were purchased from
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Published 05 Aug 2022

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

  • Durbis J. Castillo-Pazos,
  • Juan D. Lasso and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

Graphical Abstract
  • perfluoroalkylating reagent that participated in such condensation (around 30%), giving us the final yields of perfluoroalkylating reagents 1a–c displayed in Scheme 3. Afterward, to show the practicality of application of these reagents in industry, we proceeded to scale up their synthesis in gram-scale
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Published 04 Jul 2022

New synthesis of a late-stage tetracyclic key intermediate of lumateperone

  • Mátyás Milen,
  • Bálint Nyulasi,
  • Tamás Nagy,
  • Gyula Simig and
  • Balázs Volk

Beilstein J. Org. Chem. 2022, 18, 653–659, doi:10.3762/bjoc.18.66

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  • require a reduction step carried out with borane·THF complex that is used in the syntheses described in the literature but would make it difficult to scale up the process. The significance of compound (±)-9a lies in the fact that it can be converted in a known one-step reaction to compound (±)-10. The
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Published 10 Jun 2022

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

  • Martin Vrbický,
  • Karel Macek,
  • Jaroslav Pochobradský,
  • Jan Svoboda,
  • Miloš Sedlák and
  • Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

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  • epimers by recrystallization was tested. For this purpose, the nitroaldols 24 and 26 were prepared at a 10 mmol scale (ca. 4 g) using 10 mol % of the catalyst Cu(OAc)2/IV at 20 °C to achieve high yields of the products (24: 92% and 26: 84%). The nitroaldols 24 and 26 were obtained in these scale-up
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Published 14 Apr 2022

Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

  • Kian Donnelly and
  • Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

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  • approach. This entails the use of a heated packed-bed reactor filled with solid K2CO3 as a base. Using DMSO as solvent, this flow method generates the target heterocycles within short residence times of 10 minutes and in yields up to 93%. Scale-up of this flow process was achieved (34 mmol/h) and featured
  • , without the need for further extensive optimisation. Oxadiazole product 2j was chosen as the target molecule for the scale-up reaction due to the potential for further diversification via the embedded alkene. Due to the large quantity of material, an increase in column size was required to house the
  • of complex oxadiazoles. Continuous flow scale-up reaction with in-line quench and extraction. Continuous flow setup equipped with in-line extraction and purification. Screening of oxidants for cyclisation of acyl hydrazone. Optimisation of iodine-mediated cyclisation in continuous flow mode
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Published 25 Feb 2022

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

  • Thaipparambil Aneeja,
  • Cheriya Mukkolakkal Abdulla Afsina,
  • Padinjare Veetil Saranya and
  • Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

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  • proposed mechanism for the cyanation step is depicted in Scheme 21. Chemical synthesis usually needs labor-intensive and tiresome procedures. One of the approaches to overcome these challenges is to perform the reactions in flow [44]. The major advantages of this approach include predictable reaction scale
  • -up, high reproducibility and yields, lower catalyst loading, high product purity, and excellent selectivity. A visible-light-promoted Strecker-type functionalization of N-aryl-substituted tetrahydroisoquinolines under flow conditions was reported (Scheme 22) [45]. The cyanating agent utilized was
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Published 04 Jan 2022
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