Borinic Acid Catalyzed Regioselective <i>N</i>-Alkylation of Azoles
Shrey P. Desai, Matthew T. Zambri, Mark S. Taylor
Abstract
A method for regioselective N-alkylation of ambident, azole-type heterocycles with alkene or epoxide electrophiles is described. In the presence of diphenylborinic acid (Ph2BOH) and an amine cocatalyst, heterocyclic nucleophiles such as 1,2,3- and 1,2,4-triazoles, substituted tetrazoles, and purine are activated toward selective N-functionalization. The scope of electrophilic partners includes enones, 2-vinylpyridine, phenyl vinyl sulfone, a dehydroalanine derivative, and epoxides. Mechanistic studies, including in situ 11B NMR spectroscopy and kinetic analysis, are discussed.
Topics & Concepts
ChemistryRegioselectivityElectrophileNucleophileAlkylationDehydroalanineEpoxideOrganic chemistryAlkeneCatalysisCombinatorial chemistryAmino acidBiochemistryAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic ReactionsChemical Synthesis and Analysis