Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 23, Pages 8336-+Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500612
Keywords
cascade reactions; heterocycles; organocatalysis; photocatalysis
Categories
Funding
- Deutsche Forschungsgemeinschaft (DFG)
- Fonds der Chemischen Industrie (FCI, Sachbeihilfe)
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A visible light-induced photocatalytic dehydrogenation/6-cyclization/oxidation cascade converts 1-(nitromethyl)-2-aryl-1,2,3,4-tetrahydroisoquinolines into novel 12-nitro-substituted tetracyclic indolo[2,1-a]isoquinoline derivatives. Various photocatalysts promote the reaction in the presence of air and a base, the most efficient being 1-aminoanthraquinone in combination with K3PO4. Further, the 12-nitroindoloisoquinoline products can be accessed directly from C1-unfunctionalized 2-aryl-1,2,3,4-tetrahydroisoquinolines by extending the one-pot protocol with a foregoing photocatalytic cross-dehydrogenative coupling reaction, resulting in a quadruple cascade transformation.
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