Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines.
Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines.
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DOI：
10.1021/acs.joc.7b00747
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发表时间：
2017-05-19
期刊：
影响因子：
--
通讯作者：
Molander GA
中科院分区：
文献类型：
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作者：
Davies GHM;Mukhtar A;Saeednia B;Sherafat F;Kelly CB;Molander GA
描述了一种使用简单的试剂和条件从有机三氟硼酸盐和硼酸获得氮杂硼杂环酮（含羰基的硼基杂环支架）的方法。发现一种廉价的常用试剂SiO2既可作为亲氟试剂又可作为干燥剂，以促进三种不同的氮杂硼杂环丁酮平台的成环过程。对本研究中合成的一些核进行了计算分析，以将氮杂硼杂环酮与类似的碳基杂环系统进行比较。计算得出的pKa值，NICS芳香性计算，和静电势表面揭示了这些氮杂硼和它们的碳电子等排体之间的独特的等电子/isostructural关系，改变的基础上硼连接。相关的实验数据支持计算结果。
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.