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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

Abstract : A series of iron(II) complexes of N-heterocyclic carbene ligands were 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)2I 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 °C while that of the representative acetophenone substrate at a more elevated temperature of 70 °C. The benzimidazole derived complexes (1-3)b displayed superior activity than the imidazole derived (4-5)b complexes.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01121131
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Submitted on : Friday, February 27, 2015 - 3:07:50 PM
Last modification on : Friday, July 10, 2020 - 4:15:32 PM

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Dharmendra Kumar, A. P. Prakasham, Linus P. Bheeter, Jean-Baptiste Sortais, Manoj Grangwar, et al.. 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. Journal of Organometallic Chemistry, Elsevier, 2014, 762, pp.81-87. ⟨10.1016/j.jorganchem.2014.03.016⟩. ⟨hal-01121131⟩

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