Work

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

Year: 2017

Type: article

Abstract: 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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.7b00747

Authors: Geraint H. M. Davies, Asma Mukhtar, Borna Saeednia, Fatemeh Sherafat, Christopher B. Kelly, Gary A. Molander

Institutions: University of Pennsylvania, University of the Punjab, Sharif University of Technology, University of Tehran

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Higher Education Commission, Pakistan, National Institute of General Medical Sciences