Acetic Acid Promoted Metal-Free Aerobic Carbon–Carbon Bond Forming Reactions at α‑Position of Tertiary Amines

The oxidative functionalization of the benzylic C–H bonds in tetra­hydroiso­quinolines and tetrahydro-β-carboline derivatives was investigated. C–C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetra­butyl­ammonium cyanide) u...

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Bibliographic Details
Published in:Organic letters 2014-08, Vol.16 (16), p.4194-4197
Main Authors: Ueda, Hirofumi, Yoshida, Kei, Tokuyama, Hidetoshi
Format: Article
Language:English
Subjects:
Acetic Acid - chemistry
Amines - chemistry
Carbon - chemistry
Catalysis
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Tetrahydroisoquinolines - chemistry
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Summary:The oxidative functionalization of the benzylic C–H bonds in tetra­hydroiso­quinolines and tetrahydro-β-carboline derivatives was investigated. C–C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetra­butyl­ammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5018883