General and selective head-to-head dimerization of terminal alkynes proceeding via hydropalladation pathway

Claire Jahier; Olga V Zatolochnaya; Nickolay V Zvyagintsev; Valentine P Ananikov; Vladimir Gevorgyan

doi:10.1021/ol3010936

General and selective head-to-head dimerization of terminal alkynes proceeding via hydropalladation pathway

Org Lett. 2012 Jun 1;14(11):2846-9. doi: 10.1021/ol3010936. Epub 2012 May 16.

Authors

Claire Jahier¹, Olga V Zatolochnaya, Nickolay V Zvyagintsev, Valentine P Ananikov, Vladimir Gevorgyan

Affiliation

¹ Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.

PMID: 22591008
DOI: 10.1021/ol3010936

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkynes / chemical synthesis*
Alkynes / chemistry
Catalysis
Combinatorial Chemistry Techniques
Dimerization
Molecular Structure
Palladium / chemistry*
Stereoisomerism

Substances

Alkynes
Palladium