3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes

Takayuki Iwata, Mizuki Hyodo, Takumi Fujiwara, Ryusei Kawano, Leah Kuhn, Igor V. Alabugin, Mitsuru Shindo

Research output: Contribution to journalArticlepeer-review

Abstract

The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. Triple cycloaddition of ynolates to the benzyne provided 1,8,13-tris(trifluoromethyl)triptycenes with high regioselectivity. 1-Trifluoromethyltriptycenes were regioselectively obtained by the Diels-Alder reaction of anthranoxides with the benzyne. These selectivities are attributed to the electron-acceptor nature of the trifluoromethyl group on the benzyne.

Original languageEnglish
JournalSynthesis (Germany)
DOIs
Publication statusAccepted/In press - 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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