New Bis(imino)pyridine Complexes of Iron(II) and Iron(III), and Their Catalytic­ Activity in the Mukaiyama Aldol Reaction

Abstract

New iron(II) and iron(III) complexes bearing bis(imino)pyridine ligands were synthesized and successfully applied to the Mukaiyama aldol reaction. The two complexes [FeCl₂ L] (L = bis(imino)pyridine ligand, 55% isolated yield) and [LFe(μCl)₃FeCl₃] (76%) were obtained employing FeCl₂ and FeCl₃ iron sources, respectively, and characterized by elemental analyses, mass spectrometry, IR spectroscopy and, one example, by X-ray diffraction. The two new iron complexes were subsequently employed as catalysts in the Mukaiyama aldol reaction after abstraction of two chlorides by AgSbF₆ to obtain the aldol products in 43% to virtually quantitative yield (CH₂Cl₂ solvent, room temperature, 3.5 to 16 h reaction time). The impact of the oxidation state of the iron center on the reaction rate and the diastereomeric ratios of the products was investigated.

Key words

aldol reaction - catalysis - homogeneous catalysis - iron - ligands - nucleophilic addition

• References

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