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Zirconium-Mediated Cross-Coupling of Terminal Alkynes and Vinyl Bromides: Selective Synthesis of Cyclobutene and 1,3-Diene Derivatives

✍ Scribed by José Barluenga; Félix Rodríguez; Lucía Álvarez-Rodrigo; Francisco J. Fañanás

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
167 KB
Volume
10
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

A diastereoselective synthesis of 1,3‐butadiene or cyclobutene derivatives by a zirconium‐mediated reaction of alkenyllithium compounds and vinyl bromides is reported. The key steps involve the generation of zirconocene–alkyne complexes from haloalkenes and subsequent coupling with alkenyl bromides. Thus, formally the process supposes the cross‐coupling reaction between a terminal alkyne and an alkenyl bromide. Moreover, the use of butyl vinyl ether instead of vinyl bromide as the unsaturated system allows an alternative access to different 1,3‐butadiene regioisomers.

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