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: hoshi-m
chem.kitami-it.ac.jp
M. Hoshi, N. Kawamura, K. Shirakawa, Synthesis, 2006, 1961-1970.
DOI: 10.1055/s-2006-942373
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Abstract
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.
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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
