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Possible B–C bonding in the hydroboration of benzonitrile by an external electric field

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Abstract

Generally, the hydroboration of benzonitrile produces B–N containing compounds. However, an unprecedented B–C bond may be formed in the presence of a suitable external electric field (EEF). In reactions of benzonitrile with borane, when the EEF is oriented parallel to the positive direction (N → C) of the N[triple bond, length as m-dash]C bond, the barriers to Markovnikov hydroboration are decreased gradually, meaning the pathway for generating B–C bonds becomes more favorable. Accordingly, hydroboration could be influenced and its selectivity could be controlled by changing the magnitude and direction of an applied EEF.

Graphical abstract: Possible B–C bonding in the hydroboration of benzonitrile by an external electric field

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Publication details

The article was received on 29 Oct 2018, accepted on 22 Nov 2018 and first published on 23 Nov 2018


Article type: Communication
DOI: 10.1039/C8CP06704J
Citation: Phys. Chem. Chem. Phys., 2019, Advance Article
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    Possible B–C bonding in the hydroboration of benzonitrile by an external electric field

    M. Zhang and H. Xu, Phys. Chem. Chem. Phys., 2019, Advance Article , DOI: 10.1039/C8CP06704J

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