Synthesis, coordination, and catalytic application of phosphinoferrocene ligands bearing flexible thienyl and thiazolyl pendants

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F25%3A10505439" target="_blank" >RIV/00216208:11310/25:10505439 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=WYLkQylC2Z" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=WYLkQylC2Z</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d5dt02216a" target="_blank" >10.1039/d5dt02216a</a>

Result language
angličtina
Original language name
Synthesis, coordination, and catalytic application of phosphinoferrocene ligands bearing flexible thienyl and thiazolyl pendants
Original language description
Modification of the ligand backbone by introducing spacer groups alters the coordination and catalytic properties of phosphine donors. This contribution describes the synthesis of five hybrid phosphinoferrocene ligands bearing heterocyclic pendant substituents, R2PfcCH2X, where R/X = Ph/2-thienyl (1), Cy/2-thienyl (2), Ph/3-thienyl (3), Ph/5-thiazolyl (4), and Ph/2-thiazolyl (5; fc = ferrocene-1,1 -diyl, Cy = cyclohexyl). The coordination properties of these flexible donors were examined in Pd(ii) complexes. At a 1 : 2 Pd-to-ligand ratio, the reactions with a PdCl2 source uniformly gave bis(phosphine) complexes [PdCl2(L-κP)2] (L = 1-5). Upon reducing the ligand amount to 1 molar equiv., similar reactions afforded dimers [PdCl(μ-Cl)(L-κP)]2 for 1-3, the ligand-bridged dimer [(μ(P,N)-4)PdCl2]2, and the chelate complex [PdCl2(5-κ2P,N)]. The latter compound was evaluated in the Suzuki-Miyaura-type cross-coupling of aroyl chlorides with arylboronic acids, where it outperformed the benchmark catalyst [PdCl2(dppf-κ2P,P')]. The reaction was further used to prepare 3-(trifluoromethyl)benzophenone, which was converted to the drug flumecinol.
Czech name
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Czech description
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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

Project
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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