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Assessing the role of substituents in ferrocene acylphosphines and their impact on gold-catalysed reactions

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F23%3A10464671" target="_blank" >RIV/00216208:11310/23:10464671 - isvavai.cz</a>

  • Result on the web

    <a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=2fyF3EEE_6" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=2fyF3EEE_6</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1039/d3nj00201b" target="_blank" >10.1039/d3nj00201b</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Assessing the role of substituents in ferrocene acylphosphines and their impact on gold-catalysed reactions

  • Original language description

    Substituents can be used to efficiently modify the coordination and catalytic behaviour of phosphine ligands. In this article, we analyse how substituents affect the properties of ferrocene acylphosphines FcC(O)PR2 (1a-d), where PR2 is PPh2 (1a), PCy2 (1b), PAd(2) (1c) and PCg (1d; Fc = ferrocenyl, Cy = cyclohexyl, Ad = 1-adamantyl, and PCg = 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantane-8-yl). The (31)P-(77)Se scalar coupling constants 1J(PSe), determined for the corresponding phosphine selenides FcC(O)P(Se)R2 (2a-d), suggest that the basicity of the phosphine groups increases with the donor ability of the substituents R, as expected. Au(I) complexes [AuCl(1-κP)] (3a-d), obtained by replacing the dimethylsulfide ligand in [AuCl(SMe2)] with acylphosphines 1a-d, were tested in Au-catalysed alkyne hydration and intramolecular cyclisation of N-propargyl benzamide to yield 5-methylene-2-phenyl-4,5-dihydrooxazole. The collected results indicate that the highest reaction yields were generally obtained using catalysts derived from acylphosphines bearing the electron-donating aliphatic substituents 1b and 1c. From a wider perspective, the carbonyl moiety in the acylphosphines FcC(O)PR2 appears to lower steric crowding around the phosphorus atom (especially for compounds with bulky R substituents) and counterbalances the electron-donating effect of the ferrocenyl moiety.

  • 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

    10402 - Inorganic and nuclear chemistry

Result continuities

  • Project

    <a href="/en/project/GA19-09334S" target="_blank" >GA19-09334S: Uncoventional ferrocene phosphines</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2023

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    New Journal of Chemistry

  • ISSN

    1144-0546

  • e-ISSN

    1369-9261

  • Volume of the periodical

    47

  • Issue of the periodical within the volume

    9

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    11

  • Pages from-to

    4510-4520

  • UT code for WoS article

    000932668100001

  • EID of the result in the Scopus database

    2-s2.0-85148422195