B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed tandem protonation/deuteration and reduction of <i>in situ</i>-formed enamines
Rongpei Wu, Ke Gao
Abstract
A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines.
Topics & Concepts
ProtonationTandemIn situCatalysisChemistryReduction (mathematics)CrystallographyMaterials scienceIonOrganic chemistryMathematicsComposite materialGeometryOrganoboron and organosilicon chemistryBoron Compounds in ChemistryAsymmetric Hydrogenation and Catalysis