Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates

Satoshi Umezu, Gabriel dos Passos Gomes, Tatsuro Yoshinaga, Mikei Sakae, Kenji Matsumoto, Takayuki Iwata, Igor Alabugin, Mitsuru Shindo

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

We developed the novel one-pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four-step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o-benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3-symmetrical triptycenes hold promise in the design of functional materials.

Original languageEnglish
Pages (from-to)1298-1302
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number5
DOIs
Publication statusPublished - Jan 1 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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