Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

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Abstract

We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)2. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

Original languageEnglish
Pages (from-to)1440-1445
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number9
DOIs
Publication statusPublished - 5 Mar 2021

Keywords

  • Lewis acids
  • Organoboron chemistry
  • Sterically hindered compounds
  • Triptycenes

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