Isolation of a Bis(oxazol-2-ylidene)-phenylborylene adduct and its reactivity as a boron-centered nucleophile

Lingbing Kong, Yongxin Li, Rakesh Ganguly, Dragoslav Vidovic, Rei Kinjo

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111 Citations (Scopus)

Abstract

An isolable phenylborylene species supported by two oxazol-2-ylidene ligands was synthesized and structurally characterized. Computational studies revealed the presence of lone-pair electrons on the boron atom in this molecule; therefore, there are eight electrons around the three-coordinate boron center. The nucleophilic property was confirmed by the reactions with trifluoromethanesulfonic acid and [(thf)Cr(CO)5], which gave the corresponding conjugate acid and a chromium-borylene complex, respectively. Two oxazol-2-ylidene ligands effectively stabilize a phenylborylene fragment that features a lone pair of electrons on the boron atom. There are eight electrons around the tricoordinate boron center (8-B-3), and the nucleophilic boron center readily reacts with an electrophile, such as a proton or a transition-metal species, to form a boronium species and a metal-borylene complex, respectively.

Original languageEnglish
Pages (from-to)9280-9283
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number35
DOIs
Publication statusPublished - 25 Aug 2014
Externally publishedYes

Keywords

  • boron
  • borylenes
  • carbenes
  • nucleophiles
  • reactive species

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