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Inne
Synthesis and catalytic evaluation of phosphanylferrocene ligands with cationic guanidinium pendants and varied phosphane substituents.
Autorzy
Rok wydania
2019
Czasopismo
European Journal of Inorganic Chemistry
Numer woluminu
2019
Strony
4846-4854
DOI
10.1002/ejic.201901057
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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, [R2PfcCH2NHC(NH2)2]Cl (3a–d), where fc = ferrocene‐1,1′‐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){R2PfcCH2NHC(NH2)2‐κP}2]Cl2 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).
Słowa kluczowe
Phosphane ligands, Ferrocene ligands, Hydroformylation, Cross‐coupling, Palladium, Rhodium
Adres publiczny
http://dx.doi.org/10.1002/ejic.201901057
Strona internetowa wydawcy
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