Synthesis of Pyrrole-Fused Corannulenes: 1,3-Dipolar Cycloaddition of Azomethine Ylides to Corannulene

被引：56
|
作者：
Tokimaru, Yuki [1 ]
Ito, Shingo [1 ]
Nozaki, Kyoko [1 ]
机构：
[1] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1138656, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 49期
基金：
日本学术振兴会;
关键词：
azomethine ylides; corannulene; cycloaddition; polycycles; structure determination; GEODESIC POLYARENES; BOWL-INVERSION; BUCKYBOWL; CHEMISTRY; FUNCTIONALIZATION; DIHALOCARBENES; HYDROCARBONS; DERIVATIVES; TETRAANION; ACTIVATION;
D O I：
10.1002/anie.201707087
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
In the long history of corannulene chemistry, the 1,3-dipolar cycloaddition to corannulene is unprecedented. Reported herein is the 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide to corannulene, a reaction which occurs exclusively at the rim bond of corannulene, from the convex side in an exo fashion. The cycloadducts were successfully converted, by successive oxidative dehydrogenation, into pyrrole-fused corannulenes, which exhibited pronounced solvatofluorochromism.
引用
收藏
页码：15560 / 15564
页数：5
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