Organic Chemistry Portal



Construction of Terminal Conjugated Enynes: Cu-Mediated Cross-Coupling Reaction of Alkenyldialkylborane with (Trimethylsilyl)ethynyl Bromide

Masayuki Hoshi*, Noritsugu Kawamura, Kazuya Shirakawa

*Department of Applied and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, Japan, Email:

M. Hoshi, N. Kawamura, K. Shirakawa, Synthesis, 2006, 1961-1970.

DOI: 10.1055/s-2006-942373

see article for more reactions


The cross-coupling reaction of (E)- and (Z)-alk-1-enyldialkylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a catalytic amount of copper(II) acetylacetonate and a base under extremely mild conditions to provide conjugated enynes with a distal carbon-carbon triple bond.

see article for more examples

Key Words

enynes, alkenyldialkylboranes (trimethylsilyl)ethynyl bromides, cross-coupling, alk-3-en-1-ynes 1,3-bis(trimethylsilyl)alk-3-en-1-ynes

ID: J66-Y2006-1720