Jump to main content
Jump to site search

Issue 9, 2017
Previous Article Next Article

Efficient trifluoromethylation via the cyclopropanation of allenes and subsequent C–C bond cleavage

Author affiliations

Abstract

As we know, the incorporation of a trifluoromethyl group into organic molecules may significantly alter their physical and biological properties due to the high electronegativity, lipophilicity, and excellent metabolic stability of the trifluoromethyl substituent. Thus, an efficient method for the introduction of the trifluoromethyl group is of high current interest. On the other hand, vinylic cyclopropanes are a class of strained compounds capable of undergoing ring-opening reaction with other molecules. Here, CF3-substituted vinylic cyclopropanes have been highly selectively formed by a copper-catalyzed cyclic trifluoromethylation of (4,4-disubstituted-2,3-butadienyl)malonates with Togni's reagent II, in which the trifluoromethyl group was installed at the middle carbon of the allene unit by applying 1,10-phenanthroline as the ligand. Such unique cyclopropanes successfully bring the trifluoromethyl group to other useful organic skeletons by the selective cleavage of C–C bonds with an exclusive diastereoselectivity. Based on the mechanistic studies, an allene radical addition, oxidation, and allylic substitution pathway has been proposed.

Graphical abstract: Efficient trifluoromethylation via the cyclopropanation of allenes and subsequent C–C bond cleavage

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 May 2017, accepted on 22 Jun 2017 and first published on 23 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00419B
Citation: Org. Chem. Front., 2017,4, 1762-1767
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Efficient trifluoromethylation via the cyclopropanation of allenes and subsequent C–C bond cleavage

    Y. Tang, Q. Yu and S. Ma, Org. Chem. Front., 2017, 4, 1762
    DOI: 10.1039/C7QO00419B

    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.

Search articles by author

Spotlight

Advertisements