Zipper-mode double C-H activation: Palladium-catalyzed direct construction of highly-fused heterocyclic systems
Zipper-mode double C-H activation: Palladium-catalyzed direct construction of highly-fused heterocyclic systems
复制标题
DOI：
10.1021/ol702141r
复制
发表时间：
2007-11-08
期刊：
影响因子：
5.2
通讯作者：
Tanaka, Tetsuaki
中科院分区：
文献类型：
--
作者：
Ohno, Hiroaki;Iuchi, Mutsumi;Tanaka, Tetsuaki
描述了通过拉链模式的双C-H键活化直接构建稠环体系。在Cs2CO3存在下，(Z)-3-bromo-N(2-bromo-3-phenylprop-2-enyl)aniline衍生物与Pd(OAc)(2)和PCy3中心点HBF4在二氧六环中反应，以较好的产率得到4，5-萘并[3，2，1-CD]吲哚衍生物。将苯并呋喃、苯并噻吩环或吲哚基团等杂环引入到底物中，通过杂环的C-H键活化，有效地构建了高度稠合的杂环芳环体系。
Direct construction of fused aromatic ring systems by "zipper-mode" double C-H bond activation is described. Treatment of (Z)-3-bromo-N(2-bromo-3-phenylprop-2-enyl)aniline derivatives with a catalytic amount of Pd(OAc)(2) and PCy3 center dot HBF4 in the presence of Cs2CO3 in dioxane affords 4,5-naphtho[3,2,1-cd]indole derivatives in good yields. Introduction of heterocycles such as benzofuran, benzothiophene, or indole moieties into the substrates leads to the efficient construction of highly fused heterocyclic aromatic ring systems via C-H bond activation of the heteroaromatic rings.