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A New Phenoxide Chelated Ir<sup>III</sup> N‑Heterocyclic Carbene Complex and Its Application in Reductive Amination Reactions
A new
phenoxide chelated [IrÂ(NHC)ÂCp*Cl] (NHC = N-heterocyclic carbene;
Cp* = pentamethylcyclopentadienyl) complex (<b>3</b>) has been
prepared by reaction of [IrCp*Cl<sub>2</sub>]<sub>2</sub> with an
in situ prepared NHC–Ag complex in dichloromethane at ambient
temperature. The Ir<sup>III</sup> complex was stable toward air and
moisture and was fully characterized by <sup>1</sup>H, <sup>13</sup>C NMR, HRMS, and single-crystal X-ray diffraction. The new complex
was found to be an active catalyst for transfer hydrogenative reductive
amination under aqueous conditions with formate as hydrogen source
as well as hydrogenative reductive amination reactions using H<sub>2</sub>. Various carbonyl compounds such as aliphatic and aromatic
ketones and aldehydes were successfully reacted with amines to give
new amines. In comparison with transfer hydrogenative reductive amination,
the reductive amination with H<sub>2</sub> is faster and permits higher
molar ratios of the substrate to the catalyst (S/C)