Mechanochemical Transformation of CF3 Group: Synthesis of Amides and Schiff Bases

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  • Satenik Mkrtchyan
  • Michał Jakubczyk
  • Suneel Lanka
  • Muhammad Yar
  • Khurshid Ayub
  • Mohanad Shkoor
  • Pittelkow, Michael
  • Viktor O. Iaroshenko

We communicate two mild, solvent-free mechanochemical coupling transformations of CF3 group with nitro compounds into amides or Schiff bases employing Ytterbia as a catalyst. This process proceeds via C−F bond activation, accompanied with utilisation of Si-based reductants/oxygen scavengers - reductants of the nitro group. The scope and limitations of the disclosed methodologies are thoroughly studied. To the best of our knowledge, this work is the first example of mechanical energy promoted transformation of the inert CF3 group into other functionalities.

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
Volume363
Issue number24
Pages (from-to)5448-5460
Number of pages14
ISSN1615-4150
DOIs
Publication statusPublished - 2021

Bibliographical note

Funding Information:
This research project was supported by a grant from National Science Centre (NSC) Poland, the SONATA 10 (Nr. 2015/19/D/ST5/02774) obtained by Dr. Viktor Iaroshenko. The salary of Dr. Satenik Mkrtchyan was covered by a grant from National Science Centre (NSC) Poland within the framework of European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska‐Curie grant agreement Nr. 665778 (POLONEZ 2 grant, Nr. 2016/21/P/ST5/00630). Professor Michael Pittelkow appreciates the support from the Danish Council for Independent Research (DFF 4181‐00206 and 9040‐00265) and from the University of Copenhagen.

Publisher Copyright:
© 2021 Wiley-VCH GmbH

    Research areas

  • C−F bond activation, Fluorine, Mechanochemistry, Methodology, Ytterbia

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