Rhodium(I)-Catalyzed Cycloisomerization of Benzylallene-Alkynes through C-H Activation

被引：26
|
作者：
Kawaguchi, Yasuaki [1 ]
Yasuda, Shigeo [1 ]
Kaneko, Akira [1 ]
Oura, Yuki [1 ]
Mukai, Chisato [1 ]
机构：
[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 29期
关键词：
alkynes; allenes; C-H activation; cycloisomerization; rhodium; CATALYZED 5+2 CYCLOADDITIONS; BOND ACTIVATION; VINYLCYCLOPROPANES; ALLENYNES; 1ST; SELECTIVITY; CYCLIZATION; COMPLEXES; CHIRALITY; ALKENES;
D O I：
10.1002/anie.201403990
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The efficient Rh-I-catalyzed cycloisomerization of benzylallene-alkynes produced the tricyclo[9.4.0.0(3,8)]pentadecapentaene skeleton through a C-sp2-H bond activation in good yields. A plausible reaction mechanism proceeds via oxidative addition of the acetylenic C-H bond to Rh-I, an enetype cyclization to the vinylidenecarbene-Rh-I intermediate, and an electrophilic aromatic substitution with the vinylidenecarbene species. It was proposed based on deuteration and competition experiments.
引用
收藏
页码：7608 / 7612
页数：5
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