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

Yuki Tokimaru, Shingo Ito*, Kyoko Nozaki

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

58 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)15560-15564
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number49
DOIs
Publication statusPublished - Dec 4 2017
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

  • Catalysis
  • General Chemistry

Keywords

  • azomethine ylides
  • corannulene
  • cycloaddition
  • polycycles
  • structure determination

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