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Synthesis 2019; 51(17): 3214-3220
DOI: 10.1055/s-0037-1611535
DOI: 10.1055/s-0037-1611535
paper
Photoredox Fischer Indole Synthesis
This work was supported by the Kato Memorial Bioscience Foundation, a Mitsubishi Tanabe Pharma Award in Synthetic Organic Chemistry, Japan, JSPS KAKENHI Grant Numbers 23590003, 25221301, 15H05641, the Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and the Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) from the Japan Science and Technology Agency (JST).Further Information
Publication History
Received: 25 February 2019
Accepted after revision: 16 April 2019
Publication Date:
09 May 2019 (online)
Abstract
Visible light photoredox conditions were applied to the traditional Fischer indole synthesis. N,N-Diarylhydrazones were efficiently converted into the corresponding indoles even at 30 °C by treatment with bromotrichloromethane in the presence of Ru(bpy)3Cl2·6H2O as the photocatalyst. Electrochemical study revealed the viability of oxidative quenching cycle for the photocatalysis, which set the basis for proposing the redox-based reaction mechanism.
Key words
Fischer indole synthesis - [3,3]-sigmatropic rearrangement - photoredox - radicals - hydrazones - cyclic voltammetrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611535.
- Supporting Information
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