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

Authors

Pushkar Shejwalkar, University of Missouri–St. Louis
Nigam Rath, University of Missouri–St. Louis
Eike Bauer, University of Missouri–St. Louis

Document Type

Article

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.

Publication Date

November 2013

Publication Title

Synthesis

Volume

46

Issue

1

First Page

57

Last Page

66

DOI

10.1055/s-0033-1340081

Recommended Citation

Shejwalkar, Pushkar; Rath, Nigam; and Bauer, Eike, "New Bis(Imino)Pyridine Complexes of Iron(II) and Iron(III), and Their Catalytic­ Activity in the Mukaiyama Aldol Reaction" (2013). Chemistry & Biochemistry Faculty Works. 14.
DOI: https://doi.org/10.1055/s-0033-1340081
Available at: https://irl.umsl.edu/chemistry-faculty/14