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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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
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cited_by cdi_FETCH-LOGICAL-a333t-b72cb1cd1c87dc33edbbaf9e917c8f24e8cc10b36a18c470c6e50346b9aa438b3
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container_end_page 14456
container_issue 23
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container_title Journal of organic chemistry
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creator Chalotra, Neha
Ahmed, Ajaz
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description 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.
doi_str_mv 10.1021/acs.joc.8b02193
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title Photoredox Generated Vinyl Radicals: Synthesis of Bisindoles and β‑Carbolines
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