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Analytical-scale synthesis of aryl-SF4Cl via flow microfluidic technology

Analytical-scale synthesis of aryl-SF4Cl via flow microfluidic technology The SF5 group has great potential in influencing the drug-like features of organic molecules due to its chemical stability, hydrophobic surface, electron-withdrawing capability and unique octahedral geometry. However, the difficulty in synthesising SF5-containing compounds, particularly in aromatic systems, has impeded the widespread incorporation of this group into desired scaffolds in medicinal chemistry. The most troublesome step operationally involves the synthesis of the intermediate species ArSF4Cl from aryl-disulfides. Here, we report an analytical-scale synthesis of ArSF4Cl using flow microfluidic technology, allowing for safer handling of reagents and avoiding the need for gloveboxes or Cl2 cylinders. The system is fairly straightforward to prepare, clean to assemble and can be adapted easily to further developments. As well as making progress towards continuous de novo syntheses of ArSF5 compounds, this result broadly highlights the potential of flow chemistry in providing new avenues to perform challenging batch reactions.Graphical abstrac[graphic not available: see fulltext] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Analytical-scale synthesis of aryl-SF4Cl via flow microfluidic technology

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2021
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-020-00130-5
Publisher site
See Article on Publisher Site

Abstract

The SF5 group has great potential in influencing the drug-like features of organic molecules due to its chemical stability, hydrophobic surface, electron-withdrawing capability and unique octahedral geometry. However, the difficulty in synthesising SF5-containing compounds, particularly in aromatic systems, has impeded the widespread incorporation of this group into desired scaffolds in medicinal chemistry. The most troublesome step operationally involves the synthesis of the intermediate species ArSF4Cl from aryl-disulfides. Here, we report an analytical-scale synthesis of ArSF4Cl using flow microfluidic technology, allowing for safer handling of reagents and avoiding the need for gloveboxes or Cl2 cylinders. The system is fairly straightforward to prepare, clean to assemble and can be adapted easily to further developments. As well as making progress towards continuous de novo syntheses of ArSF5 compounds, this result broadly highlights the potential of flow chemistry in providing new avenues to perform challenging batch reactions.Graphical abstrac[graphic not available: see fulltext]

Journal

Journal of Flow Chemistry – Springer Journals

Published: Jan 7, 2021

References

  • Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules
    S Altomonte, M Zanda
  • Preparation and utility of organic pentafluorosulfanyl-containing compounds
    PR Savoie, JT Welch
  • Synthesis and biological evaluation of analogues of the kinase inhibitor nilotinib as Abl and kit inhibitors
    DY Duveau, X Hu, MJ Walsh, S Shukla, AP Skoumbourdis, MB Boxer, SV Ambudkar, M Shen, CJ Thomas
  • Next generation of fluorine-containing pharmaceuticals, compounds currently in phase II-III clinical trials of major pharmaceutical companies: new structural trends and therapeutic areas
    Y Zhou, J Wang, Z Gu, S Wang, W Zhu, JL Acenã, VA Soloshonok, K Izawa, H Liu
  • Pentafluorosulfanyl as a novel building block for enzyme inhibitors: Trypanothione reductase inhibition and antiprotozoal activities of diarylamines
    B Stump, C Eberle, WB Schweizer, M Kaiser, R Brun, RL Krauth-Siegel, D Lentz, F Diederich
  • Synthesis and biological evaluation of the first pentafluorosulfanyl analogs of mefloquine
    P Wipf, T Mo, SJ Geib, D Caridha, GS Dow, L Gerena, N Roncal, EE Milner
  • The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine
    JT Welch, DS Lim
  • Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): beginning of a new era of “super-trifluoromethyl” arene chemistry and its industry
    T Umemoto, LM Garrick, N Saito
  • Making the SF5 group more accessible: a gas-reagent-free approach to aryl Tetrafluoro-λ 6 -sulfanyl chlorides
    CR Pitts, D Bornemann, P Liebing, N Santschi, A Togni
  • A unified strategy for Arylsulfur(VI) fluorides from aryl halides: access to Ar-SOF3 compounds
    Wang L, Cornella J
  • Synthesis and characterization of 2-pyridylsulfur pentafluorides
    OS Kanishchev, WR Dolbier
  • An improved method for the fluorination of arylsulfur chlorotetrafluorides to arylsulfur pentafluorides
    K Lummer, MV Ponomarenko, GV Röschenthaler, M Bremer, P Beier
  • Silver-induced self-immolative cl-F exchange fluorination of arylsulfur chlorotetrafluorides: synthesis of arylsulfur pentafluorides
    B Cui, S Jia, E Tokunaga, N Saito, N Shibata
  • The Hitchhiker’s guide to flow chemistry
    MB Plutschack, B Pieber, K Gilmore, PH Seeberger
  • Microreactors for elemental fluorine
    RD Chambers, RCH Spink
  • Diacetoxyiodobenzene mediated oxidative transformation of thione to disulfides
    SJ Singh, NS Devi
  • A laboratory-scale continuous flow chlorine generator for organic synthesis
    FJ Strauss, D Cantillo, J Guerra, CO Kappe
  • Crown ether metal complex fluoride salt as a facile and low hygroscopic fluoride source for nucleophilic fluorination
    VH Jadhav, HJ Jeong, W Choi, DW Kim
  • Alkyl- and Arylsulfur Trifluorides
    WA Sheppard
  • Disposable cartridge concept for on-demand synthesis of Turbo Grignards, Knochel-Hauser Amides and Magnesium Alkoxides
    M Berton, K Sheehan, A Adamo, DT McQuade
  • Metal-free Photocatalytic aerobic oxidation of Thiols to disulfides in batch and continuous-flow
    A Talla, B Driessen, NJW Straathof, LG Milroy, L Brunsveld, V Hessel, T Noël