Visible light mediated homo- and heterocoupling of benzyl alcohols and benzyl amines on polycrystalline cadmium sulfide

Mitkina, Tatiana and Stanglmair, Christoph and Setzer, Wolfgang and Gruber, Michael and Kisch, Horst and Koenig, Burkhard (2012) Visible light mediated homo- and heterocoupling of benzyl alcohols and benzyl amines on polycrystalline cadmium sulfide. ORGANIC & BIOMOLECULAR CHEMISTRY, 10 (17). pp. 3556-3561. ISSN 1477-0520, 1477-0539

Full text not available from this repository. (Request a copy)

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.

Item Type: Article
Uncontrolled Keywords: OXIDATIVE C-C; PHOTOREDOX CATALYSIS; SEMICONDUCTOR PHOTOCATALYSIS; HYDROGEN-PRODUCTION; ORGANIC-SYNTHESIS; AROMATIC KETONES; AQUEOUS-SOLUTION; SCHIFF-BASES; BONDS; PHOTOADDITION;
Subjects: 500 Science > 540 Chemistry & allied sciences
600 Technology > 610 Medical sciences Medicine
Divisions: Medicine > Lehrstuhl für Anästhesiologie
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 25 May 2020 08:47
Last Modified: 25 May 2020 08:47
URI: https://pred.uni-regensburg.de/id/eprint/19508

Actions (login required)

View Item View Item