Enhanced enantioselective oxidation of olefins catalyzed by Mn-porphyrin immobilized on graphene oxide

An efficient enantioselective heterogeneous catalyst, GO-[Mn(TPyP)tart], was prepared by covalent attachment of Mn(III) complex of H2TPyP via the propyl linkage to graphene oxide (GO) nanosheet and using chiral tartrate counter ion. The catalyst was characterized by Fourier transform infrared (FT-IR...

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Bibliographic Details
Published in:Tetrahedron 2018-05, Vol.74 (18), p.2202-2210
Main Authors: Berijani, Kayhaneh, Farokhi, Afsaneh, Hosseini-Monfared, Hassan, Janiak, Christoph
Format: Article
Language:English
Subjects:
Asymmetric epoxidation
Enantioselectivity
Graphene oxide nanosheets
Heterogeneous catalyst
Manganese-porphyrin
Oxygen
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Summary:An efficient enantioselective heterogeneous catalyst, GO-[Mn(TPyP)tart], was prepared by covalent attachment of Mn(III) complex of H2TPyP via the propyl linkage to graphene oxide (GO) nanosheet and using chiral tartrate counter ion. The catalyst was characterized by Fourier transform infrared (FT-IR), diffuse reflectance ultraviolet–visible (DR UV–Vis) spectroscopy, powder X-ray diffraction (XRD), scanning electron microscopy (SEM), Raman and thermogravimetric analysis (TGA). The graphene-supported Mn-porphyrin showed higher activity for the enantioselective epoxidation of unfunctionalized olefins with molecular oxygen in the presence of isobutyraldehyde. It could be recovered easily and reused in asymmetric oxidation of styrene precursor in a five-step sequence without any considerable loss of its catalytic activity and selectivity. The obtained optically epoxide selectivities were achieved in 86% to 100%. [Display omitted] •A simple and highly efficient enantioselective catalyst, GO-[Mn(TPyP)tart], was developed.•The catalyst could oxidize olefins with 58–100% ee, epoxide selectivity 86–100% and TOF up to 14792.•The catalyst is heterogeneous and stable which could be recycled at least 5 times.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.03.027