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Synthesis 2018; 50(15): 2897-2907
DOI: 10.1055/s-0036-1592006
DOI: 10.1055/s-0036-1592006
special topic
Methylene Blue-Catalyzed Oxidative Cleavage of N-Carbonylated Indoles
Authors
T.W. is grateful to the University at Albany, State University of New York, for financial support. P. L. thanks the National Science Foundation (CHE-1654122) for financial support.
Weitere Informationen
Publikationsverlauf
Received: 27. Januar 2018
Accepted after revision: 09. April 2018
Publikationsdatum:
08. Mai 2018 (online)
Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis
Abstract
The development of a visible-light-mediated oxidative cleavage of electron-deficient indoles is reported. Methylene blue serves as an effective catalyst and the transformation shows a broad substrate scope. A variety of functional groups are well accommodated in the mild reaction conditions. The photo-mediated single electron transfer and oxidative cleavage mechanisms were investigated via density functional theory and Marcus theory calculations.
Key words
methylene blue - visible light - electron-deficient indoles - Witkop–Winterfeldt oxidation - photocatalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1592006.
- Supporting Information (PDF)
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