Directed copper-catalyzed C-H functionalization of unactivated olefins with azodicarbonamide compounds

The copper-catalyzed strategy employing the 8-aminoquinoline directing group has proven to be a highly advantageous approach for functionalizing C-H bonds. In this study, we present the successful application of this strategy to accomplish Heck-type coupling reactions and construct β-lactam skeleton...

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Bibliographic Details
Published in:RSC advances 2024-08, Vol.14 (38), p.27475-2748
Main Authors: Cui, Jing, Wang, Xiaoya, Zeng, Runsheng
Format: Article
Language:English
Subjects:
Alkenes
Amides
Aminoquinolines
Chemical bonds
Chemical reactions
Chemistry
Copper
Functional groups
Substrates
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Summary:The copper-catalyzed strategy employing the 8-aminoquinoline directing group has proven to be a highly advantageous approach for functionalizing C-H bonds. In this study, we present the successful application of this strategy to accomplish Heck-type coupling reactions and construct β-lactam skeletons, simultaneously introducing a unique cyano functional group. The resulting Heck-type coupling products demonstrate good stereo- and region-selectivity. Initial mechanistic investigations indicate that the reaction proceeds via a radical coupling mechanism, exhibiting a wide substrate scope and delivering good yields. The copper-catalyzed strategy employing directing group has proven to be a advantageous approach. In this study, we present the successful application of this strategy to accomplish Heck-type coupling reactions and construct β-lactam skeletons.
ISSN:2046-2069
2046-2069
DOI:10.1039/d4ra04113e