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Cationic iron(II) complexes of the mixed cyclopentadienyl (Cp) and the N-heterocyclic carbene (NHC) ligands as effective precatalysts for the hydrosilylation of carbonyl compounds

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Title Cationic iron(II) complexes of the mixed cyclopentadienyl (Cp) and the N-heterocyclic carbene (NHC) ligands as effective precatalysts for the hydrosilylation of carbonyl compounds
 
Creator KUMAR, D
PRAKASHAM, AP
BHEETER, LP
SORTAIS, JB
GANGWAR, M
ROISNEL, T
KALITA, AC
DARCEL, C
GHOSH, P
 
Subject Iron
NHC ligands
Benzimidazole
Imidazole
Hydrosilylation
RING-OPENING POLYMERIZATION
CROSS-COUPLING REACTIONS
H BOND ACTIVATION
ARYL GRIGNARD-REAGENTS
EFFICIENT HYDROSILYLATION
CATALYZED HYDROSILYLATION
GOLD(I) COMPLEXES
SELECTIVE HYDROSILYLATION
TRANSFER HYDROGENATION
COMPUTATIONAL INSIGHT
 
Description A series of iron(II) complexes of N-heterocyclic carbene ligands was synthesized and fully structurally characterized. Specifically, the benzimidazole based {Cp[1,3-di-R-benzimidazol-2-ylidene]-Fe(CO)(2)}I [R = Et (1b), i-Pr (2b) and n-Bu (3b)] and the imidazole based {Cp[1-benzyl-3-R-imidazol-2-ylidene] Fe(CO)(2)}PF6 [R - Me (4b) and Et (5b)] type of complexes were synthesized from their respective benzimidazolium iodide (1-3)a and their imidazolium hexafluorophosphate (4-5)a salts by the reaction with CpFe(CO)(2)I in the presence of MN(SiMe3)(2) (M = Li or K) as a base. The molecular structures of the (1-5)b complexes reveal that the metal center display a conventional piano stool structure. More importantly, the (1-5)b complexes, when irradiated with visible light, effectively catalyzed the hydrosilylation reaction of carbonyl compounds namely, of the aldehyde and ketone substrates, using organosilane reagents. Specifically, the (1-5)b complexes performed the hydrosilylation of a representative benzaldehyde substrate using phenylsilane in ambient conditions at 30 degrees C while that of the representative acetophenone substrate at a more elevated temperature of 70 degrees C. The benzimidazole derived complexes (1-3)b displayed superior activity than the imidazole derived (4-5)b complexes. (C) 2014 Elsevier B. V. All rights reserved.
 
Publisher ELSEVIER SCIENCE SA
 
Date 2014-12-28T15:23:57Z
2014-12-28T15:23:57Z
2014
 
Type Article
 
Identifier JOURNAL OF ORGANOMETALLIC CHEMISTRY, 76281-87
0022-328X
1872-8561
http://dx.doi.org/10.1016/j.jorganchem.2014.03.016
http://dspace.library.iitb.ac.in/jspui/handle/100/16864
 
Language English