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2-Aminopyrazine-functionalized MCM-41 nanoporous silica as a new efficient heterogeneous ligand for Cu-catalyzed allylic C–H bonds oxidation of olefins

  • Saadi SamadiEmail author
  • Akram Ashouri
  • Shadi Kamangar
  • Fatemeh Pourakbari
Article
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Abstract

In spite of the importance of the application of allylic C–H bond oxidation of olefins in organic synthesis and existence of the numerous reports, lots of limitations such as large excess of the olefin respect to the oxidant, low chemical yield, long time of reaction and a large amount of the catalyst were reminded. We introduced a novel catalytic system using functionalized MCM-41 as catalyst support to promote efficiency of this reaction. The heterogeneous ligand Pyr-MCM-41 was prepared by substituted 2-aminopyrazine ligand on functionalized MCM-41 with 3-chloropropyltrimthoxysilane and characterized by FT-IR, XRD, SEM, EDX, BET, TGA, CHN techniques. In situ immobilized Pyr-MCM-41 by copper (I) trifluoromethanesulfonate (CuOTf) was applied in direct catalytic esterification of inert C–H bonds in olefins using various peresters at room temperature.

Keywords

2-Aminopyrazine MCM-41 In situ immobilized Olefin Allylic C–H bond oxidation Copper trifluoromethanesulfonate Allylic esters 

Notes

Acknowledgements

We are grateful to the University of Kurdistan Research Councils and the Iranian National Science Foundation (Proposal No: 95838133) for the partial support of this work.

Supplementary material

11164_2019_3967_MOESM1_ESM.docx (11 mb)
Supplementary Material (included materials and characterization methods, the typical procedure, FT-IR, 1HNMR and 13CNMR spectra for synthesized compounds 3–10, the typical procedure and scanning electron micrographs of MCM-41 and Cl-MCM-41) associated with this article can be found in the online version (DOCX 11263 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Saadi Samadi
    • 1
    Email author
  • Akram Ashouri
    • 1
  • Shadi Kamangar
    • 1
  • Fatemeh Pourakbari
    • 1
  1. 1.Laboratory of Asymmetric Synthesis, Department of Chemistry, Faculty of ScienceUniversity of KurdistanSanandajIran

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