Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes

Tatsuro Yoshinaga, Takumi Fujiwara, Takayuki Iwata, Mitsuru Shindo

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

1,8,13-Trialkyl(aryl)silyl-9-hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3-silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step-by-step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13-trihalogenated triptycenes were then converted to 1,8,13-functionalized triptycenes.

Original languageEnglish
Pages (from-to)13855-13859
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number61
DOIs
Publication statusPublished - Nov 4 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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