Remote C-H Selenylation of 8-Amidoquinolines via Copper-Catalyzed Radical Cross-Coupling

A copper‐catalyzed regioselective C–H selenylation of quinolines with readily available diaryl diselenides is developed based on a chelation‐controlled radical cross‐coupling strategy. The reaction is scalable, tolerates a wide spectrum of functional groups, and proceeds with excellent C5 regioselec...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-09, Vol.2016 (25), p.4321-4327
Main Authors: Sahoo, Harekrishna, Mandal, Anup, Selvakumar, Jayaraman, Baidya, Mahiuddin
Format: Article
Language:English
Subjects:
C-H activation
Copper
Electrons
Homogeneous catalysis
Quinolines
Radical reactions
Selenylation
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Summary:A copper‐catalyzed regioselective C–H selenylation of quinolines with readily available diaryl diselenides is developed based on a chelation‐controlled radical cross‐coupling strategy. The reaction is scalable, tolerates a wide spectrum of functional groups, and proceeds with excellent C5 regioselectivity to deliver selenoquinolines in high yields (up to 98 %). A single electron transfer (SET) mediated mechanism is proposed. An efficient chelation‐controlled radical cross‐coupling under copper catalysis is described for highly C5‐regioselective selenylation of quinolines with diaryl diselenides (yields up to 98 % and 39 examples).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600772