Synthesis, coordination behavior, and catalytic properties of dppf congeners with an inserted carbonyl moiety
Identifikátory výsledku
Kód výsledku v 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>
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Synthesis, coordination behavior, and catalytic properties of dppf congeners with an inserted carbonyl moiety
Popis výsledku v původním jazyce
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.
Název v anglickém jazyce
Synthesis, coordination behavior, and catalytic properties of dppf congeners with an inserted carbonyl moiety
Popis výsledku anglicky
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.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10402 - Inorganic and nuclear chemistry
Návaznosti výsledku
Projekt
<a href="/cs/project/GA19-09334S" target="_blank" >GA19-09334S: Nekonvenční ferrocenové fosfiny</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2022
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
New Journal of Chemistry
ISSN
1144-0546
e-ISSN
1369-9261
Svazek periodika
46
Číslo periodika v rámci svazku
45
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
17
Strana od-do
21536-21552
Kód UT WoS článku
000862868400001
EID výsledku v databázi Scopus
2-s2.0-85140431258