Regioselective 1,4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation
Royal Society of Chemistry (RSC)
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Keyzer, E., Kang, S. S., Hanf, S., & Wright, D. (2017). Regioselective 1,4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation. Chemical Communications, 53 (68), 9434-9437. https://doi.org/10.1039/C7CC04988A
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.
E. N. K. thanks NSERC of Canada for a PGSD as well as the Cambridge Commonwealth, European, and International Trust and Gonville and Caius College for funding.
External DOI: https://doi.org/10.1039/C7CC04988A
This record's URL: https://www.repository.cam.ac.uk/handle/1810/278012