Synlett 2013; 24(5): 587-590
DOI: 10.1055/s-0032-1318271
letter
© Georg Thieme Verlag Stuttgart · New York

Z-Selective Dimerization of Aromatic Terminal Alkynes Catalyzed by an Iridium(I)–N-Heterocyclic Carbene–Phosphine System

Calum D. Forsyth
Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland, UK   Fax: +44(141)5484246   Email: w.kerr@strath.ac.uk
,
William J. Kerr*
Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland, UK   Fax: +44(141)5484246   Email: w.kerr@strath.ac.uk
,
Laura C. Paterson
Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland, UK   Fax: +44(141)5484246   Email: w.kerr@strath.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 10 January 2013

Accepted after revision: 30 January 2013

Publication Date:
18 February 2013 (online)


Abstract

The development of an iridium-catalyzed regio- and stereoselective dimerization process has enabled the formation of (Z)-enyne products. More specifically, low catalyst loadings of an iridium(I) complex, featuring a bulky N-heterocyclic carbene–phosphine ligand combination, has been successfully employed in this selective head-to-head dimerization of terminal alkynes via C–H activation.

 
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