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Issue 68, 2017
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Regioselective 1,4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation

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Abstract

The reaction of the commercially available ammonium salt NH4BPh4 with a pyridine-activated pinacolborane species generates a boronium cation that facilitates the 1,4-selective hydroboration of pyridines in polar solvents. This catalytic reaction is amenable to a host of reactive functional groups and provides access to sterically bulky hydroboration products, previously inaccessible by metal-free routes. Further, the regioselectivity of this reaction can be altered by reducing the polarity of the reaction solvent, resulting in greater proportions of the 1,2-hydroboration product.

Graphical abstract: Regioselective 1,4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation

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Publication details

The article was received on 28 Jun 2017, accepted on 21 Jul 2017 and first published on 21 Jul 2017


Article type: Communication
DOI: 10.1039/C7CC04988A
Citation: Chem. Commun., 2017,53, 9434-9437
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    Regioselective 1,4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation

    E. N. Keyzer, S. S. Kang, S. Hanf and D. S. Wright, Chem. Commun., 2017, 53, 9434
    DOI: 10.1039/C7CC04988A

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