Highly regioselective [2+2+2] cycloaddition of terminal alkynes catalyzed by titanium complexes of p-tert-butylthiacalix[4]arene

Naoya Morohashi, Katsuya Yokomakura, Tetsutaro Hattori, Sotaro Miyano

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Mono- and dinuclear titanium complexes of p-tert-butylthiacalix[4]arene were applied as a catalyst for [2+2+2] cycloaddition of terminal alkynes. They showed high catalytic activity and regioselectivity toward 1,3,5-trisubstituted benzenes over 1,2,4-trisubstituted isomers. The regioselectivity was rationalized in terms of the steric effect of the thiacalixarene skeleton and the coordination of the bridging sulfur atom to the titanium center.

Original languageEnglish
Pages (from-to)1157-1161
Number of pages5
JournalTetrahedron Letters
Volume47
Issue number7
DOIs
Publication statusPublished - 2006 Feb 13

Keywords

  • Alkyne cyclotrimerization
  • Calixarene
  • Titanium complex

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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