Synthesis of Phosphanylferrocenecarboxamides Bearing Guanidinium Substituents and Their Application in the Palladium-Catalyzed Cross-Coupling of Boronic Acids with Acyl Chlorides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F17%3A10338364" target="_blank" >RIV/00216208:11310/17:10338364 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejic.201600461" target="_blank" >http://dx.doi.org/10.1002/ejic.201600461</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejic.201600461" target="_blank" >10.1002/ejic.201600461</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of Phosphanylferrocenecarboxamides Bearing Guanidinium Substituents and Their Application in the Palladium-Catalyzed Cross-Coupling of Boronic Acids with Acyl Chlorides
Original language description
Phosphanylferrocene donors bearing polar guanidinium substituents, namely acylguanidinium chloride, [Ph(2)PfcCONHC(NH2)NH2]Cl (1), and amidoguanidinium chloride, [Ph(2)PfcCONHCH(2)CH(2)NHC(NH2)NH2]Cl (2; fc = ferrocene-1,1-diyl), have been prepared and characterized. As functional phosphane donors, they were employed in the synthesis of Pd-II complexes bearing 2-[(dimethylamino)methyl-kappa N]phenyl-kappa C-1 (L-NC) and (3)-allyl supporting ligands, [(L-NC)PdCl(L-kappa P)] and [(eta(3)-C3H5)PdCl(L-P)] (L = 1 and 2), respectively. These defined complexes as well as their surrogates generated in situ from the respective palladium(II) precursor and the phosphanylferrocene ligand were evaluated as catalysts for the coupling of boronic acids with acyl chlorides to give ketones in an aqueous biphasic system. The coupling reaction proceeded best with a simple catalyst formed from Pd(OAc)(2) and ligand 2, which (at 0.2 mol-% Pd loading) produced substituted benzophenones from benzoyl chlorides and benzeneboronic acids in very good yields. These yields could then be further improved by a proper choice of the reaction partners. Analogous reactions involving aliphatic substrates generally afforded lower yields.
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/GA13-08890S" target="_blank" >GA13-08890S: Polar ferrocene amidophosphine ligands for catalytic applications</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
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
2
Country of publishing house
DE - GERMANY
Number of pages
9
Pages from-to
288-296
UT code for WoS article
000393404400014
EID of the result in the Scopus database
2-s2.0-85010304110