Photoinduced Copper-Catalyzed Regioselective Synthesis of Indoles: Three-Component Coupling of Arylamines, Terminal Alkynes, and Quinones

The first successful example of a visible‐light‐induced copper‐catalyzed process for CH annulation of arylamines with terminal alkynes and benzoquinone is described. This three‐component reaction allows use of a variety of commercial terminal alkynes as coupling partners for the one‐step regioselec...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-11, Vol.54 (47), p.13896-13901
Main Authors: Sagadevan, Arunachalam, Ragupathi, Ayyakkannu, Hwang, Kuo Chu
Format: Article
Language:English
Subjects:
annulations
copper
heterocycles
photochemistry
radicals
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Summary:The first successful example of a visible‐light‐induced copper‐catalyzed process for CH annulation of arylamines with terminal alkynes and benzoquinone is described. This three‐component reaction allows use of a variety of commercial terminal alkynes as coupling partners for the one‐step regioselective synthesis of functionalized indoles. Moreover, the current process represents a sustainable and atom‐economical approach for the preparation of complex indoles from easily accessible starting materials under visible‐light irradiation, without the need for expensive metals and harsh reaction conditions. Visibility: A facile visible‐light initiated copper‐catalyzed process leads to regioselectively functionalized indoles by the CH annulation of simple arylamines with terminal alkynes and benzoquinone at room temperature. This transformation represents a sustainable and atom‐economical approach for the preparation of substituted indoles from readily available substrates.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201506579