title: Visible light mediated homo- and heterocoupling of benzyl alcohols and benzyl amines on polycrystalline cadmium sulfide.
abstract: The oxidative coupling of sp(3) hybridized carbon atoms by photocatalysis is a valuable synthetic method as stoichiometric oxidation reagents can be avoided and dihydrogen is the only byproduct of the reaction. Cadmium sulfide, a readily available semiconductor, was used as a visible light heterogeneous photocatalyst for the oxidative coupling of benzyl alcohols and benzyl amines by irradiation with blue light. Depending on the structure of the starting material, good to excellent yields of homocoupling products were obtained as mixtures of diastereomers. Cross-coupling between benzyl alcohols and benzyl amines gave product mixtures, but was selective for the coupling of tetrahydroisoquinolines to nitromethane. The results demonstrate that CdS is a suitable visible light photocatalyst for oxidative bond formation under anaerobic conditions.
authors.affiliation: Department of Chemistry and Pharmacy, Universität Regensburg, Universitätsstraße 31, 93040 Regensburg, Germany.
authors.forename: Tatiana
authors.initials: T
authors.lastname: Mitkina
authors.forename: Christoph
authors.initials: C
authors.lastname: Stanglmair
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Setzer
authors.forename: Michael
authors.initials: M
authors.lastname: Gruber
authors.forename: Horst
authors.initials: H
authors.lastname: Kisch
authors.forename: Burkhard
authors.initials: B
authors.lastname: König
mesh_terms: D000588:Amines / Q000737:chemistry*; D019905:Benzyl Alcohol / Q000737:chemistry*; D019187:Cadmium Compounds / Q000737:chemistry*; D008027:Light; D008958:Models, Molecular; D008968:Molecular Conformation; D055668:Photochemical Processes; D013440:Sulfides / Q000737:chemistry*; D013696:Temperature
chemical_list: D000588:Amines; D019187:Cadmium Compounds; D013440:Sulfides; C034939:cadmium sulfide; D019905:Benzyl Alcohol