Palladium-catalyzed Sonogashira coupling of amides: access to ynones via C-N bond cleavage

The first palladium-catalyzed Sonogashira coupling of amides has been developed, which proceeds via a selective cleavage of the N-acylsaccharin C-N bond. Notably, the new approach employs N-acylsaccharins as coupling partners to give ynones in good to excellent yield. This protocol can be efficientl...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (81), p.12076-12079
Main Authors: Cui, Ming, Wu, Hongxiang, Jian, Junsheng, Wang, Hui, Liu, Chao, Daniel, Stelck, Zeng, Zhuo
Format: Article
Language:English
Subjects:
Amides
Arrays
Bonding
Catalysts
Cleavage
Coupling
Palladium
Synthesis (chemistry)
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Summary:The first palladium-catalyzed Sonogashira coupling of amides has been developed, which proceeds via a selective cleavage of the N-acylsaccharin C-N bond. Notably, the new approach employs N-acylsaccharins as coupling partners to give ynones in good to excellent yield. This protocol can be efficiently utilized in the synthesis of a broad array of ynones under low catalyst loading and Cu-free conditions.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc06428k