Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 17, Pages 3556-3561Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob07053g
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Funding
- Alexander von Humboldt Foundation
- Deutsche Forschungsgemeinschaft [GRK 1626]
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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.
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