Synthesis of macrocyclic heteroarylenes by consecutive inter- and intramolecular cycloadditions of thiophenylene-tethered triynes

Takanori Shibata*, Masako Fujimoto, Takashi Otani

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Consecutive inter- and intramolecular [2+2+2] cycloadditions of various thiophenylene-tethered triynes were comprehensively studied by using chiral Rh catalysts. When we started from 2,3- and 3,4-thiophenylene-tethered substrates, dimerization proceeded and chiral tetraheteroarylenes were obtained. In contrast, reactions of 2,5-thiophenylene-tethered substrates gave hexaheteroarylenes as trimers. When bis- and tris(2,5-thiophenylene)-tethered triynes were used, mixtures of dimers and trimers were obtained, which included macrocyclic systems that contained up to 12 aromatic rings, and their photophysical properties were measured.

Original languageEnglish
Pages (from-to)8453-8461
Number of pages9
JournalTetrahedron
Volume70
Issue number45
DOIs
Publication statusPublished - 2014 Nov 11

Keywords

  • Asymmetric synthesis
  • Chirality
  • Cycloaddition
  • Heteroarylenes
  • Macrocycles
  • Rhodium
  • Thiophene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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