Synthesis and Catalytic Evaluation of Phosphanylferrocene Ligands with Cationic Guanidinium Pendants and Varied Phosphane Substituents
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F19%3A10404415" target="_blank" >RIV/00216208:11310/19:10404415 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=B1pD7Bi3qw" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=B1pD7Bi3qw</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejic.201901057" target="_blank" >10.1002/ejic.201901057</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and Catalytic Evaluation of Phosphanylferrocene Ligands with Cationic Guanidinium Pendants and Varied Phosphane Substituents
Original language description
This contribution expands the still narrow class of functional ferrocene phosphanes with polar cationic groups, focusing on the synthesis and catalytic use of a series of phosphanylferrocene ligands bearing positively charged guanidinium tags, [R(2)PfcCH(2)NHC(NH2)(2)]Cl (3a-d), where fc = ferrocene-1,1 '-diyl, R = isopropyl (a), cyclohexyl (b), phenyl (c), and 2-furyl (d). To probe the influence of phosphane substituents, these compounds were studied as supporting ligands in Pd-catalyzed Suzuki-Miyaura cross-coupling of acyl chlorides with arylboronic acids, in analogous coupling of aryl bromides with arylboronic acids, and in Rh-catalyzed hydroformylation of 1-hexene using trans-[RhCl(CO){R(2)PfcCH(2)NHC(NH2)(2)-kappa P}(2)]Cl-2 complexes (4a-d) as pre-catalysts. The outcome of the cross-coupling reactions strongly depended on the starting materials, and no ligand generated a universally applicable catalyst when combined with Pd(OAc)(2). In the hydroformylation reactions, the catalyst based on 4d led to lower conversions than all others, which performed rather similarly. Overall, the phenyl-substituted phosphane 3c emerged as a good compromise, giving rise to reasonably efficient and stable catalysts in most cases (except for Suzuki-Miyaura biaryl cross-couplings, wherein electron-rich alkylphosphanes performed better than 3c).
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
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
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 Inorganic Chemistry
ISSN
1434-1948
e-ISSN
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Volume of the periodical
Neuveden
Issue of the periodical within the volume
45
Country of publishing house
DE - GERMANY
Number of pages
9
Pages from-to
4846-4854
UT code for WoS article
000498447600001
EID of the result in the Scopus database
2-s2.0-85075758155