Catalytic and asymmetric synthesis of heteroatom-containing cyclic polyarylenes

Research output: Contribution to journalArticle

Abstract

Cyclic polyarylene is a series of compounds, where the cyclic structure is constructed by a number of phenylene and/or heteroarylene moieties. Cyclic polyarylenes consisting of more than three arylene moieties are non-planar, and introduction of substituent (s) induces axial chirality. We comprehensively studied catalytic and enantioselective synthesis of various cyclic polyphenylenes by consecutive inter- and intramolecular cycloadditions of triynes, where 1,6-diyne and alkyne moieties were tethered by phenylene moiety. We further used this strategy for the construction of cyclic heteroarylenes using thiophene-tethered triynes. Next, we focused on the enantioselective construction of sulfur-containing benzo-fused medium ring systems. For examples, intermolecular cycloaddition of 1,8-diynes tethered by sulfur and two ortho-phenylene moieties with an alkyne gave axially chiral poly-substituted tribenzothiepins possessing a seven-membered ring core. We succeeded in the enantioselective synthesis of seven to eleven-membered benzo-fused compounds by intramolecular reaction of triynes consisting of sulfur-tethered 1,6-diyne and 1, «-diyne moieties (n = 8—11).

Original languageEnglish
Pages (from-to)1005-1013
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume77
Issue number10
DOIs
Publication statusPublished - 2019

Keywords

  • Axial chirality
  • Cyclic polyarylene
  • Cycloaddition
  • Enantioselective synthesis
  • Heteroatom

ASJC Scopus subject areas

  • Organic Chemistry

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