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Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines

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journal contribution
posted on 09.05.2017, 18:07 by Geraint H. M. Davies, Asma Mukhtar, Borna Saeednia, Fatemeh Sherafat, Christopher B. Kelly, Gary A. Molander
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.