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

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 – reduct...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-12, Vol.363 (24), p.5448-5460
Main Authors: Mkrtchyan, Satenik, Jakubczyk, Michał, Lanka, Suneel, Yar, Muhammad, Ayub, Khurshid, Shkoor, Mohanad, Pittelkow, Michael, Iaroshenko, Viktor O.
Format: Article
Language:English
Subjects:
Amides
Coupling (molecular)
C−F bond activation
Fluorine
Imines
Mechanochemistry
Methodology
Nitro compounds
Reducing agents
Transformations
Ytterbia
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100538