Synthesis of a Polar Phosphinoferrocene Amidosulfonate Ligand and Its Application in Pd-Catalyzed Cross-Coupling Reactions of Aromatic Boronic Acids and Acyl Chlorides in an Aqueous Medium
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10328032" target="_blank" >RIV/00216208:11310/16:10328032 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/acs.organomet.6b00600" target="_blank" >http://dx.doi.org/10.1021/acs.organomet.6b00600</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.organomet.6b00600" target="_blank" >10.1021/acs.organomet.6b00600</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of a Polar Phosphinoferrocene Amidosulfonate Ligand and Its Application in Pd-Catalyzed Cross-Coupling Reactions of Aromatic Boronic Acids and Acyl Chlorides in an Aqueous Medium
Original language description
The reaction of [1'-(diphenylphosphino)ferrocenyl]methylamine (1), generated in situ from its hydrochloride and triethylamine, with 2-sulfobenzoic anhydride afforded an anionic phosphino-amide, which was isolated as a triethylammonium salt, Ph2PfcCH2NHCOC6H4SO3(HNEt3) (2; fc = ferrocene-1,1'-diyl). A similar reaction of 1 with phthalic anhydride only furnished the salt (Ph2PfcCH2NH3)[C6H4CO2H(CO2)]. When it was reacted with [PdCl2(MeCN)(2)] and [(LPd)-Pd-NC(mu-Cl)](2) (L(NC) = 2-[(dimethylamino-kappaN)methyl]phenyl-kappaC-1), compound 2 gave rise to the bisphosphine complex [PdCl2(2-kappa P)2] and the bridge-cleavage product [L(NC)PdCl(2-kappa P)], respectively. An analogue of the latter complex containing 2'-amino-[1,1'-biphenyl]-2-yl-kappaN-2,C-2 as the auxiliary chelating ligand, compound 8, was prepared in a similar manner from 2 and the respective Pd precursor. Finally, the reaction of 2 with [L(NC)Pd(acac)] proceeded with the replacement of the acetylacetonate ligand (acac), affording a dipalladium complex featuring two phosphinosulfonate anions as the O,P-bridges, [L(NC)Pd(mu(P,O)-Ph2PfcCH2NHCOC6H4SO3)](2), which was structurally characterized by single-crystal X-ray diffraction analysis. All of these Pd(II) complexes, especially compound 8, formed active catalysts for Pd-mediated cross-coupling of aromatic boronic acids with benzoyl chlorides to produce substituted benzophenones in toluene (benzene) water biphasic mixtures. This particular coupling reaction was employed during the preparation of 4'-chloro-4-hydroxybenzophenone, which was in turn converted to fenofibrate, a generic drug widely used to reduce cholesterol levels in blood.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CA - Inorganic chemistry
OECD FORD branch
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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
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organometallics
ISSN
0276-7333
e-ISSN
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Volume of the periodical
35
Issue of the periodical within the volume
19
Country of publishing house
US - UNITED STATES
Number of pages
10
Pages from-to
3378-3387
UT code for WoS article
000385209400016
EID of the result in the Scopus database
2-s2.0-84991203749