Regioselective 1,4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation
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Peer-reviewed
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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.
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3402 Inorganic Chemistry, 3405 Organic Chemistry, 34 Chemical Sciences
Journal Title
Chemical Communications
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Journal ISSN
1359-7345
1364-548X
1364-548X
Volume Title
53
Publisher
Royal Society of Chemistry (RSC)
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Engineering and Physical Sciences Research Council (EP/K039520/1)
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.