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Issue 10, 2015
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Visible-light photoredox catalysis: direct synthesis of fused β-carbolines through an oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade in batch and flow microreactors

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Abstract

Fused β-carbolines were synthesized via a visible light photoredox catalyzed oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade in batch and flow microreactors. Several structurally diverse heterocyclic scaffolds were obtained in good yields by coupling of tetrahydro-β-carbolines with a variety of dipolarophiles under photoredox multiple C–C bond forming events. The photoredox coupling of tetrahydro-β-carboline with 1,4-benzoquinone was significantly faster in continuous flow microreactors and the desired products were obtained in higher yields compared to batch reactors.

Graphical abstract: Visible-light photoredox catalysis: direct synthesis of fused β-carbolines through an oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade in batch and flow microreactors

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Supplementary files

Article information


Submitted
01 Jul 2015
Accepted
13 Aug 2015
First published
14 Aug 2015

Org. Chem. Front., 2015,2, 1308-1312
Article type
Research Article
Author version available

Visible-light photoredox catalysis: direct synthesis of fused β-carbolines through an oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade in batch and flow microreactors

D. Chandrasekhar, S. Borra, J. S. Kapure, G. S. Shivaji, G. Srinivasulu and R. A. Maurya, Org. Chem. Front., 2015, 2, 1308
DOI: 10.1039/C5QO00207A

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