Photoredox Generated Vinyl Radicals: Synthesis of Bisindoles and β‑Carbolines

A photoredox catalyzed approach enabling use of alkynes as surrogate of 2-oxoaldehydes/1,2-diones is reported. The method overcomes the difficulty associated with application of unsubstituted aliphatic α-oxoaldehydes, which has hitherto limited their general use. Indoles, tryptamine, and tryptophan...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-12, Vol.83 (23), p.14443-14456
Main Authors: Chalotra, Neha, Ahmed, Ajaz, Rizvi, Masood Ahmad, Hussain, Zakir, Ahmed, Qazi Naveed, Shah, Bhahwal Ali
Format: Article
Language:English
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Summary:A photoredox catalyzed approach enabling use of alkynes as surrogate of 2-oxoaldehydes/1,2-diones is reported. The method overcomes the difficulty associated with application of unsubstituted aliphatic α-oxoaldehydes, which has hitherto limited their general use. Indoles, tryptamine, and tryptophan methyl ester participated in the reaction to give a variety of α-oxo based analogues. Quantum yield investigations support a radical chain mechanism.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02193