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Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F20%3A00524181" target="_blank" >RIV/67985858:_____/20:00524181 - isvavai.cz</a>

  • Alternative codes found

    RIV/44555601:13440/20:43895557

  • Result on the web

    <a href="http://hdl.handle.net/11104/0309759" target="_blank" >http://hdl.handle.net/11104/0309759</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/ejoc.202000273" target="_blank" >10.1002/ejoc.202000273</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification

  • Original language description

    A series of new highly fluorophilic ionic liquids ( f > 110) was synthetized from 3‑iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8‐tridecafluorooctyl)silane and N‐alkyl imidazoles, followed by anion exchange. N‐heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification ( umpolung ) of cinnamaldehyde with alcohols. The most effective N‐methyl derivative with iodide as a counter anion was studied in detail with respect to the optimization of reaction conditions, substrate scope and recyclability. Recovery of the precatalyst was achieved using either fluorous extraction or performing the reaction in suitable fluorous biphase system with direct recycling of the fluorinated precatalyst phase. For both tested options, the catalytic activity did not significantly decrease within 5 subsequent cycles. The redox esterification was shown to proceed also in supercritical carbon dioxide (scCO 2 ) as an alternative solvent where the activity of the fluorinated catalyst was also superior to the nonfluorinated model, while retaining the benefit of easy recycling.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

    <a href="/en/project/EF17_048%2F0007411" target="_blank" >EF17_048/0007411: UniQSurf - Centre of biointerfaces and hybrid functional materials</a><br>

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2020

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    European Journal of Organic Chemistry

  • ISSN

    1434-193X

  • e-ISSN

  • Volume of the periodical

    2020

  • Issue of the periodical within the volume

    24

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    9

  • Pages from-to

    3591-3598

  • UT code for WoS article

    000538770500001

  • EID of the result in the Scopus database

    2-s2.0-85086030389