91347-87-4Relevant articles and documents
Zirconium-Mediated Cross-Coupling of Terminal Alkynes and Vinyl Bromides: Selective Synthesis of Cyclobutene and 1,3-Diene Derivatives
Barluenga, Jose,Rodriguez, Felix,Alvarez-Rodrigo, Lucia,Fananas, Francisco J.
, p. 101 - 108 (2007/10/03)
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.