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Chirally-Modified Graphite Oxide as Chirality Inducing Support for Asymmetric Epoxidation of Olefins with Grafted Manganese Porphyrin

  • Elahe Ahadi
  • Hassan Hosseini-MonfaredEmail author
  • Carsten Schlüsener
  • Christoph Janiak
  • Afsaneh Farokhi
Article
  • 16 Downloads

Abstract

A chirality inducer was prepared by graphite oxide (GO) functionalization with enantiopure l-tartrate (GO*) and used as asymmetric support for a covalently-linked manganese porphyrine complex [Mn(TPyP)OAc]. The thereby obtained heterogeneous catalyst, GO*-[Mn(TPyP)OAc], showed excellent performance and ee-values of 92–99% for the asymmetric epoxidation of prochiral olefins with O2 as oxidant and isobutyraldehyde as co-reductant in acetonitrile; linear terminal olefins with 54–76% conversion and quantitative conversion of aromatic olefins. The GO*-[Mn(TPyP)OAc] catalyst is highly active, recyclable, and at the same time simple and inexpensive to prepare with a chiral inducer from the chiral pool. The structure of the catalyst was elucidated by scanning electron microscopy (SEM), transmission electron microscopy (TEM), BET analysis, FT-IR, Raman, and photoluminescence spectroscopic methods.

Graphic Abstract

Graphite oxide functionalized with an enantiopure group was used as a chirality inducer and asymmetric support for a Mn-porphyrine complex. The thereby obtained heterogeneous catalyst is an excellent enantioselective catalyst for the epoxidation of prochiral olefins.

Keywords

Chiral epoxidation Oxygen Manganese porphyrin Graphite oxide Heterogeneous catalysis 

Notes

Acknowledgements

The University of Zanjan is acknowledged for financial support. We thank the Center for Advanced Imaging (CAi) and Sophia Köhler of the Institut für Kolloide und Nanooptik of the Heinrich-Heine-Universität Düsseldorf for their support in obtaining the TEM images.

Supplementary material

10562_2019_2933_MOESM1_ESM.docx (5.9 mb)
Supplementary material 1 (DOCX 6016 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of ZanjanZanjanIran
  2. 2.Department of ChemistryAmirkabir University of TechnologyTehranIran
  3. 3.Institut für Anorganische Chemie und StrukturchemieHeinrich-Heine-UniversitätDüsseldorfGermany

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