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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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&apos;)]. The reaction was further used to prepare 3-(trifluoromethyl)benzophenone, which was converted to the drug flumecinol.

Název v anglickém jazyce

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

Popis výsledku anglicky

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&apos;)]. The reaction was further used to prepare 3-(trifluoromethyl)benzophenone, which was converted to the drug flumecinol.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

—

Návaznosti

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

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Dalton Transactions

ISSN

1477-9226

e-ISSN

1477-9234

Svazek periodika

54

Číslo periodika v rámci svazku

44

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

18

Strana od-do

16611-16628

Kód UT WoS článku

001601584200001

EID výsledku v databázi Scopus

2-s2.0-105021344498