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
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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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