Jump to main content
Jump to site search

Issue 6, 2015
Previous Article Next Article

Generation of 1,2-azaboretidines via reduction of ADC borane adducts

Author affiliations

Abstract

Reaction of the acyclic (diamino)carbene (ADC) :C(NiPr2)2 (1) with different dihaloboranes of the type RBX2 (R = Mes, Dur; X = Cl, Br) smoothly afforded a novel class of ADC-stabilized borane adducts. For MesBBr2 however, the reaction did not stop at the adduct level, but an uncommon rearrangement process occurred, which eventually resulted in the formation of a 5-membered boracycle after elimination of mesitylene. Chemical reduction of the ADC borane adducts by KC8 selectively yielded air stable 1,2-azaboretidines. Detailed DFT studies suggest a reduction mechanism involving a highly reactive borylene intermediate, which is converted into the boracycles via a rearrangement/C–H activation sequence.

Graphical abstract: Generation of 1,2-azaboretidines via reduction of ADC borane adducts

Back to tab navigation

Supplementary files

Publication details

The article was received on 25 Mar 2015, accepted on 16 Apr 2015 and first published on 16 Apr 2015


Article type: Edge Article
DOI: 10.1039/C5SC01077B
Citation: Chem. Sci., 2015,6, 3461-3465
  • Open access: Creative Commons BY license
  •   Request permissions

    Generation of 1,2-azaboretidines via reduction of ADC borane adducts

    H. Braunschweig, A. Gackstatter, T. Kupfer, T. Scheller, F. Hupp, A. Damme, N. Arnold and W. C. Ewing, Chem. Sci., 2015, 6, 3461
    DOI: 10.1039/C5SC01077B

    This article is licensed under a Creative Commons Attribution 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.

    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