Aerobic α‐Oxidation of N‐Substituted Tetrahydroisoquinolines to Dihydroisoquinolones via Organo‐photocatalysis

An efficient visible‐light‐induced α‐oxidation of N‐substituted tetrahydroisoquinolines to dihydroisoquinolones has been developed using eosin Y as an organo‐photocatalyst and oxygen as a green oxidant. The reactions were carried out under mild reaction conditions; the desired dihydroisoquinolones w...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 361; no. 5; pp. 1124 - 1129
Main Authors Aganda, Kim Christopher C., Hong, Boseok, Lee, Anna
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 05.03.2019
Wiley Subscription Services, Inc
Subjects
aerobic oxidation
Chemistry
Chemistry, Applied
Chemistry, Organic
dihydroisoquinolones
lactams
Oxidation
Photocatalysis
photoredox catalysis
Physical Sciences
Science & Technology
Substitutes
Substrates
SUPPORTED GOLD NANOPARTICLES
TERTIARY-AMINES
aerobic oxidation
C-H FUNCTIONALIZATION
dihydroisoquinolones
BENZYLIC AMINES
lactams
VISIBLE-LIGHT
SYNTHETIC APPLICATIONS
photoredox catalysis
BOND ACTIVATION
EFFICIENT
CYCLIC AMINES
MOLECULAR-OXYGEN
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Summary:An efficient visible‐light‐induced α‐oxidation of N‐substituted tetrahydroisoquinolines to dihydroisoquinolones has been developed using eosin Y as an organo‐photocatalyst and oxygen as a green oxidant. The reactions were carried out under mild reaction conditions; the desired dihydroisoquinolones were obtained in up to 96% yield at room temperature under oxygen atmosphere. This transformation provides a convenient route to dihydroisoquinolones with a wide range of substrates.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801301