4.7 Article

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

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 24, Pages 5448-5460

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100538

Keywords

Fluorine; Ytterbia; Mechanochemistry; C-F bond activation; Methodology

Funding

  1. National Science Centre (NSC) Poland within European Union's Horizon 2020 research and innovation programme under the Marie Skodowska-Curie grant [665778, 2016/21/P/ST5/00630]
  2. Danish Council for Independent Research [DFF 4181-00206, 9040-00265]
  3. University of Copenhagen
  4. National Science Centre (NSC) Poland, the SONATA 10 [2015/19/D/ST5/02774]

Ask authors/readers for more resources

In this study, two mild, solvent-free mechanochemical coupling transformations of CF3 group with nitro compounds were successfully demonstrated, leading to amides or Schiff bases. Ytterbia was used as a catalyst to facilitate the process, which involves C-F bond activation and the use of Si-based reductants/oxygen scavengers. This work represents the first example of utilizing mechanical energy to promote the transformation of the inert CF3 group into other functionalities.
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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available