A Visible Light Photocatalytic Cross-Dehydrogenative Coupling/Dehydrogenation/6-Cyclization/Oxidation Cascade: Synthesis of 12-Nitroindoloisoquinolines from 2-Aryltetrahydroisoquinolines

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...

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Bibliographic Details
Published inChemistry : a European journal Vol. 21; no. 23; pp. 8336 - 8340
Main Authors Rusch, Fabian, Unkel, Lisa-Natascha, Alpers, Dirk, Hoffmann, Frank, Brasholz, Malte
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.06.2015
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
cascade reactions
organocatalysis
OXIDATION
CATALYSIS
heterocycles
COUPLING REACTIONS
NITROENAMINES
photocatalysis
FACILE
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201500612