Ullmann coupling reaction of 1,3-bistriflate esters of calix[4]arenes: facile syntheses of monoaminocalix[4]arenes and 4,4′:6,6′-diepithiobis(phenoxathiine)

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Abstract

Treatment of 1,3-bistriflate esters of thiacalix- (6a) and calix[4]arenes 6b with benzylamine in the presence of CuI and K3PO4 results in the displacement of a TfO moiety with a benzylamino group, which provides an easy access to monoaminothiacalix[4]arene 4a and its methylene-bridged counterpart 4b. On the other hand, the reaction of 6a in the absence of benzylamine leads to intramolecular dietherification, giving 4,4′:6,6′-diepithiobis(phenoxathiine) 7a.

Original languageEnglish
Pages (from-to)7660-7664
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number43
DOIs
Publication statusPublished - 2007 Oct 22

Keywords

  • Aminocalixarenes
  • Intramolecularly-bridged calixarene
  • Ullmann coupling reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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