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Journal of Materials Science

, Volume 54, Issue 9, pp 6908–6916 | Cite as

Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral BINOL-functionalized nanoporous graphene oxides

  • Xu Wang
  • Jiahui Guo
  • Fengxiang Qie
  • Yong YanEmail author
Chemical routes to materials
  • 215 Downloads

Abstract

The supporting material on which an asymmetric catalytic reaction takes place has proved to be an important component which could influence the efficiency and sometimes enantioselectivity of a heterogeneous asymmetric reaction. On the other hand, graphene oxide (GO) has attracted broad attentions because of its unique characteristics and potential applications in many fields. However, GOs have been rarely employed as the supporting materials for heterogeneous catalytic reactions, especially those enantioselective reactions. Herein, a new type of GO-based heterogeneous catalyst was prepared for enantioselective addition of diethylzinc to aromatic aldehydes. To produce this GO catalyst, commercial GO was firstly oxidized in an acidic environment to make nanoporous GOs and then enantiopure (R) or (S)-NH2-BINOLs were attached (covalently) onto the nanoporous GOs, and this GO-BINOL was subsequently treated by using Ti(OiPr)4. The as-prepared GO-BINOL-Ti catalyst displayed good reactivity (99%) and modest enantioselectivity (45% ee) in the following asymmetric addition reactions. We expect this preliminary demonstration could inspire the research by using GO as heterogeneous catalytic supports and could improve the enantioselectivity later.

Notes

Acknowledgements

We acknowledge the financial support from the Ministry of Science and Technology of China (No. 2016YFA0203400) and the Chinese Academy of Sciences.

Compliance with ethical standards

Conflict of interest

There are no conflicts to declare.

Supplementary material

10853_2018_3230_MOESM1_ESM.docx (1.4 mb)
Supplementary material 1 (DOCX 1384 kb)

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Copyright information

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

Authors and Affiliations

  1. 1.CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in NanoscienceNational Center for Nanoscience and TechnologyBeijingChina
  2. 2.University of Chinese Academy of SciencesBeijingChina

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