Pushing the Lewis Acidity Boundaries of Boron Compounds With Non‐Planar Triarylboranes Derived from Triptycenes

Research output: Contribution to journalArticle

Abstract

Bending the planar trigonal boron center of triphenylborane by connecting its aryl rings with carbon or phosphorus linkers gave access to a series of 9-boratriptycene derivatives with unprecedented structures and reactivities. NMR spectroscopy and X-ray diffraction of the Lewis adducts of these non-planar boron Lewis acids with weak Lewis base revealed particularly strong covalent bond formation. The first Lewis adduct of a trivalent boron compounds with the Tf 2N anion illustrates the unrivaled Lewis acidity of these species. Increasing the pyramidalization of the boron center and using a cationic phosphonium linker resulted in an exceptional enhancement of Lewis acidity. Introduction of a phosphorus and a boron atom at each edge of a triptycene framework, allowed access to new bifunctional Lewis acid-base 9-phospha-10-boratriptycenes featuring promising reactivity for the activation of carbon-halogen bonds.

Original languageEnglish
Pages (from-to)16889-16893
Number of pages5
JournalAngewandte Chemie International Edition
Volume58
Issue number47
DOIs
Publication statusPublished - 18 Nov 2019

Keywords

  • boron
  • Lewis acids
  • Lewis superacid
  • non-planar
  • triarylboranes

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