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Issue 10, 2018
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Super electron donors derived from diboron

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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

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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
Chem. Sci., 2018,9, 2711-2722
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Super electron donors derived from diboron

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

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