Jump to main content
Jump to site search

Issue 10, 2018
Previous Article Next Article

Super electron donors derived from diboron

Author affiliations

Abstract

Single-electron transfer is an important process in organic chemistry, in which a single-electron reductant (electron donor) acts as a key component. Compared with metal-based electron donors, organic electron donors have some unique advantages, such as tunable reduction ability and mild reaction conditions. The development of novel organic electron donors with good reduction ability together with ease of preparation is in high demand. Based on the pyridine-catalyzed radical borylation reaction developed in our laboratory, we have discovered that, the reaction system consisting of a diboron(4) compound, methoxide and a pyridine derivative could smoothly produce super electron donors in situ. Two boryl–pyridine based species, the major one being a trans-2H,2′H-[2,2′-bipyridine]-1,1′-diide borate complex and the minor one being a pyridine radical anion–borate complex, were observed and carefully characterized. These complexes were found to be organic super electron donors unprecedented in literature, and their formation mechanisms were studied by DFT calculations. The diboron/methoxide/pyridine system enables the preparation of organic super electron donors from easily accessible starting materials under mild conditions, which has the potential to be a general and practical single-electron reducing agent in organic synthesis.

Graphical abstract: Super electron donors derived from diboron

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Jan 2018, accepted on 28 Jan 2018 and first published on 12 Feb 2018


Article type: Edge Article
DOI: 10.1039/C8SC00008E
Citation: Chem. Sci., 2018,9, 2711-2722
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Super electron donors derived from diboron

    L. Zhang and L. Jiao, Chem. Sci., 2018, 9, 2711
    DOI: 10.1039/C8SC00008E

    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