Palladium-Catalyzed Addition of 1,3-Diones to Ynamides: An Entry to Alkoxy-Substituted Enamides

A new metal‐catalyzed addition reaction of 1,3‐diketones to ynamides, which provides access to unprecedented alkoxy‐substituted enamides, is disclosed herein. A screening of catalytic systems showed that both a phosphapalladacycle and a cationic gold complex were capable of promoting this reaction r...

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Bibliographic Details
Published in:ChemCatChem 2014-09, Vol.6 (9), p.2544-2548
Main Authors: Graux, Lionel V., Clavier, Hervé, Buono, Gérard
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
enamines
nucleophilic addition
Organic chemistry
palladium
reaction mechanisms
ynamides
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Summary:A new metal‐catalyzed addition reaction of 1,3‐diketones to ynamides, which provides access to unprecedented alkoxy‐substituted enamides, is disclosed herein. A screening of catalytic systems showed that both a phosphapalladacycle and a cationic gold complex were capable of promoting this reaction rapidly and cleanly. The scope investigation revealed that variously substituted terminal ynamides and cyclic 1,3‐diones were well tolerated. The use of internal ynamides led to the formation of both E and Z isomers with low to good selectivities. The proposed mechanism suggests that the phosphapalladacycle acts as a π Lewis acid to activate the ynamide. Get it together: A new metal‐catalyzed addition reaction of 1,3‐diketones to ynamides providing an access to unprecedented alkoxy‐substituted enamides is disclosed. After optimization of the reaction conditions and the catalytic system, the scope investigation revealed a broad applicability to numerous ynamides and cyclic 1,3‐diones.
ISSN:1867-3880
1867-3899
1867-3899
DOI:10.1002/cctc.201402398