Synthesis, coordination behavior, and catalytic properties of dppf congeners with an inserted carbonyl moiety
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F22%3A10452534" target="_blank" >RIV/00216208:11310/22:10452534 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=i7VDGRtejw" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=i7VDGRtejw</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d2nj04270c" target="_blank" >10.1039/d2nj04270c</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis, coordination behavior, and catalytic properties of dppf congeners with an inserted carbonyl moiety
Original language description
Ferrocene phosphines have been extensively studied as ligands for coordination chemistry and catalysis. Among the vast number of compounds reported to date, 1,1'-bis(diphenylphosphino)ferrocene (dppf) still holds a prominent place due to its versatile coordination behavior and wide catalytic applications. This paper describes the synthesis of four semihomologous dppf congeners with a carbonyl spacer inserted between the ferrocene unit and one of the phosphine moieties, R(2)PfcC(O)PR'(2) (R/R' = Ph/Ph, Ph/Cy, Cy/Ph and Cy/Cy; Cy = cyclohexyl and fc = ferrocene-1,1'-diyl). These compounds were prepared from the respective borane-protected phosphinocarboxylic acids R(2)PfcCO(2)H.BH3 by chlorination with oxalyl chloride, reaction with HPR'(2)/NEt(3) and subsequent removal of the protecting group. The compounds were further converted to selenides R2P(Se)fcC(O)P(Se)R'(2) to evaluate their electronic properties through the (1)J(PSe) coupling constants. In addition, two series of palladium complexes were prepared, viz. the Pd(II) chelate complexes cis-[PdCl2(R(2)PfcC(O)PR'(2)-κ(2)P,P')] and the Pd(0) complexes [Pd(η(2)-mi)(R(2)PfcC(O)PR'(2)-κ(2)P,P')] (mi = N-methylmaleimide). The latter compounds were applied as catalysts for the Stille cross-coupling reaction of 4-fluorobenzoyl chloride with phenyl-tributylstannane to produce 4-fluorobiphenyl. The best catalytic results were obtained with the [Pd(η(2)-mi)(Ph(2)PfcC(O)PPh2-κ(2)P,P')] complex that contained the least electron-rich ligand.
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
2022
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
46
Issue of the periodical within the volume
45
Country of publishing house
GB - UNITED KINGDOM
Number of pages
17
Pages from-to
21536-21552
UT code for WoS article
000862868400001
EID of the result in the Scopus database
2-s2.0-85140431258