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Azaborininones: synthesis and structural analysis of a carbonyl-containing class of azaborines

Davies, G. H. M ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1021/acs.joc.7b00747
  3. Abstract:
  4. An approach to access azaborininones (carbonyl-containing, boron-based heterocyclic scaffolds) using simple reagents and conditions from both organotrifluoroborates and boronic acids is described. An inexpensive, common reagent, SiO2, was found to serve as both a fluorophile and desiccant to facilitate the annulation process across three different azaborininone platforms. Computational analysis of some of the cores synthesized in this study was undertaken to compare the azaborininones with the analogous carbon-based heterocyclic systems. Computationally derived pKa values, NICS aromaticity calculations, and electrostatic potential surfaces revealed a unique isoelectronic/isostructural relationship between these azaborines and their carbon isosteres that changed based on boron connectivity. Correlation to experimentally derived data supports the computational findings. © 2017 American Chemical Society
  5. Keywords:
  6. Boron ; Driers (materials) ; Organic compounds ; Scaffolds ; Aromaticities ; Boronic acid ; Carbon-based ; Computational analysis ; Derived data ; Electrostatic potential surface ; Heterocyclic systems ; Synthesis (chemical) ; Boronic acid derivative ; Carbon ; Carbonyl derivative ; Calculation ; Chemical bond ; Structure analysis ; Substitution reaction ; Surface property ; Synthesis
  7. Source: Journal of Organic Chemistry ; Volume 82, Issue 10 , 2017 , Pages 5380-5390 ; 00223263 (ISSN)
  8. URL: https://pubs.acs.org/doi/10.1021/acs.joc.7b00747