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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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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Abstract 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.
AbstractList A visible light-induced photocatalytic dehydrogenation/6π-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.
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.
Author Brasholz, Malte
Alpers, Dirk
Rusch, Fabian
Unkel, Lisa-Natascha
Hoffmann, Frank
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Issue 23
Keywords cascade reactions
organocatalysis
OXIDATION
CATALYSIS
heterocycles
COUPLING REACTIONS
NITROENAMINES
photocatalysis
FACILE
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Snippet A visible light-induced photocatalytic dehydrogenation/6-cyclization/oxidation cascade converts 1-(nitromethyl)-2-aryl-1,2,3,4-tetrahydroisoquinolines into...
A visible light-induced photocatalytic dehydrogenation/6π-cyclization/oxidation cascade converts 1-(nitromethyl)-2-aryl-1,2,3,4-tetrahydroisoquinolines into...
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SubjectTerms Chemistry
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Physical Sciences
Science & Technology
Title A Visible Light Photocatalytic Cross-Dehydrogenative Coupling/Dehydrogenation/6-Cyclization/Oxidation Cascade: Synthesis of 12-Nitroindoloisoquinolines from 2-Aryltetrahydroisoquinolines
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Volume 21
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