Synthesis of 1,1,4,4-tetrabromo-2-butenes and related compounds via desilylation-bromination of silylated 1,3-butadiene derivatives.
The combination of zirconocene-mediated coupling of silylated alkynes with a protonation-desilylation or bromination-desilylation process afforded otherwise unavailable butadiene derivatives. When (E,E)-2,3-dialkyl-1,4-bis(trimethylsilyl)-1,3-butadienes were treated with 3 equiv of Br(2) in CH(2)Cl(2), (E)-2,3-dialkyl-1,1,4,4-tetrabromo-2-butenes were obtained in excellent yields with perfect stereoselectivity.
Xi
Zhenfeng
Z
Peking University-Hokkaido University Joint Lab, College of Chemistry, Peking University, Beijing 100871, China.
Liu
Xiaozhong
X
Lu
Jianming
J
Bao
Fengyu
F
Fan
Hongtao
H
Li
Zhiping
Z
Takahashi
Tamotsu
T