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

页码：15560 / 15564

页数：5

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