Regioselective 1, 4-hydroboration of pyridines catalyzed by an acid-initiated boronium cation. Issue 68 (9th August 2017)

• Record Type: Journal Article
• Authors: Keyzer, Evan N.; Kang, Sky S.; Hanf, Schirin; Wright, Dominic S.
• Is Part Of: Chemical communications. Volume 53:Issue 68(2017)
• Page Start: 9434
• Page End: 9437
• Publication Date: 2017-08-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc04988a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A simple methodology for the 1, 4-regioselective hydroboration of pyridines has been developed using NH4 BPh4 to initiate a borocation-catalyzed reaction. Abstract : The reaction of the commercially available ammonium salt NH4 BPh4 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.