Anti-Markovnikov Hydroamination of Alkenes with Aqueous Ammonia by Metal-Loaded Titanium Oxide Photocatalyst
So-Yeong Park, Jaeyoung Jeong, Ken‐ichi Fujita, Akira Yamamoto, Hisao Yoshida
Abstract
A completely new route was established to synthesize valuable primary amines from alkenes by using aqueous ammonia, that is, a simple photocatalytic hydroamination of alkenes using aqueous ammonia with a metal-loaded TiO2 photocatalyst. Although the photochemical hydroamination prefers to form amines according to the Markovnikov rule, the new photocatalytic hydroamination gives anti-Markovnikov products predominantly. With an Au-loaded TiO2 photocatalyst, the amine yield reached up to 93% and the regioselectivity of anti-Markovnikov products was above 98%. The reaction mechanism was proposed for the new photocatalytic hydroamination.
Topics & Concepts
HydroaminationMarkovnikov's ruleChemistryPhotocatalysisAqueous solutionRegioselectivityAminationAmmoniaAmine gas treatingOrganic chemistryCatalysisCombinatorial chemistryPhotochemistryAdvanced Photocatalysis TechniquesTiO2 Photocatalysis and Solar CellsAdvanced Nanomaterials in Catalysis