Boron-substituted 1,3-dihydro-1,3-azaborines: Synthesis, structure, and evaluation of aromaticity

  • Senmiao Xu
  • , Tanya C. Mikulas
  • , Lev N. Zakharov
  • , David A. Dixon
  • , Shih Yuan Liu*
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

Abstract

Getting the family together: A general synthetic strategy based on nucleophilic substitution provided B-substituted 1,3-dihydro-1,3-azaborines (see scheme), BN isosteres of arenes with potential for application in biomedicine and materials science. Experimental structural analysis and calculations suggest that the aromaticity of the 1,3-dihydro-1,3-azaborine heterocycle is intermediate between that of benzene and that of 1,2-dihydro-1,2-azaborine.

Original languageEnglish
Pages (from-to)7527-7531
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number29
DOIs
StatePublished - 15 Jul 2013
Externally publishedYes

Keywords

  • aromaticity
  • azaborines
  • boron
  • heterocycles
  • synthetic methods

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