Synthesis and Catalytic Evaluation of Phosphanylferrocene Ligands with Cationic Guanidinium Pendants and Varied Phosphane Substituents

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and Catalytic Evaluation of Phosphanylferrocene Ligands with Cationic Guanidinium Pendants and Varied Phosphane Substituents

Popis výsledku v původním jazyce

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 &apos;-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).

Název v anglickém jazyce

Synthesis and Catalytic Evaluation of Phosphanylferrocene Ligands with Cationic Guanidinium Pendants and Varied Phosphane Substituents

Popis výsledku anglicky

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 &apos;-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).

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

2019

Kód důvěrnosti údajů

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

Název periodika

European Journal of Inorganic Chemistry

ISSN

1434-1948

e-ISSN

—

Svazek periodika

Neuveden

Číslo periodika v rámci svazku

45

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

4846-4854

Kód UT WoS článku

000498447600001

EID výsledku v databázi Scopus

2-s2.0-85075758155