Jump to main content
Jump to site search


Defluorosilylation of trifluoromethane: upgrading an environmentally damaging fluorocarbon

Author affiliations

Abstract

The rapid, room-temperature defluorosilylation of trifluoromethane, a highly potent greenhouse gas, has been achieved using a simple silyl lithium reagent. An extensive computational mechanistic analysis provides a viable reaction pathway and demonstrates the unexpected electrophilic nature of LiCF3. The reaction generates a bench stable fluorinated building block that shows promise as an easy-to-use difluoromethylating agent. The difluoromethyl group is an increasingly important bioisostere in active pharmaceutical ingredients, and therefore our methodology creates value from waste. The potential scalability of the process has been demonstrated by achieving the reaction on a gram-scale.

Graphical abstract: Defluorosilylation of trifluoromethane: upgrading an environmentally damaging fluorocarbon

Back to tab navigation

Supplementary files

Article information


Submitted
16 Aug 2020
Accepted
17 Sep 2020
First published
17 Sep 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

Defluorosilylation of trifluoromethane: upgrading an environmentally damaging fluorocarbon

D. J. Sheldon, G. Coates and M. R. Crimmin, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC04592F

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements