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Synthesis of Pyrrole‐Fused Corannulenes: 1,3‐Dipolar Cycloaddition of Azomethine Ylides to Corannulene
Author(s) -
Tokimaru Yuki,
Ito Shingo,
Nozaki Kyoko
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707087
Subject(s) - corannulene , cycloaddition , chemistry , pyrrole , azomethine ylide , dehydrogenation , fullerene , photochemistry , 1,3 dipolar cycloaddition , computational chemistry , combinatorial chemistry , organic chemistry , catalysis
Abstract 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.