General and Selective Head-to-Head Dimerization of Terminal Alkynes Proceeding via Hydropalladation Pathway

General and Selective Head-to-Head Dimerization of Terminal Alkynes Proceeding via Hydropalladation Pathway

A general highly regio- and stereoselective palladium-catalyzed head-to-head dimerization reaction of terminal acetylenes is presented. This methodology allows for the efficient synthesis of a variety of 1,4-enynes as single E stereoisomers. Computational studies reveal that this dimerization reacti...

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Veröffentlicht in:Organic letters 2012-06, Vol.14 (11), p.2846-2849
Hauptverfasser: Jahier, Claire, Zatolochnaya, Olga V, Zvyagintsev, Nickolay V, Ananikov, Valentine P, Gevorgyan, Vladimir
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Dimerization
Molecular Structure
Palladium - chemistry
Stereoisomerism
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Zusammenfassung:A general highly regio- and stereoselective palladium-catalyzed head-to-head dimerization reaction of terminal acetylenes is presented. This methodology allows for the efficient synthesis of a variety of 1,4-enynes as single E stereoisomers. Computational studies reveal that this dimerization reaction proceeds via the hydropalladation pathway.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3010936