Boron-Substituted 1,3-Dihydro-1,3-azaborines: Synthesis, Structure, and Evaluation of Aromaticity


  • Correspondence concerning X-ray crystallography should be directed to L.N.Z. ( Correspondence concerning electronic-structure calculations should be directed to D.A.D. This research was supported by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM094541). Funding for the University of Oregon Chemistry Research and Instrumentation Services has been furnished in part by the NSF (CHE-0923589).


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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.