Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components.
Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components.
复制标题
DOI：
10.1021/acs.joc.6b00435
复制
发表时间：
2016-05-06
期刊：
影响因子：
--
通讯作者：
Molander GA
中科院分区：
文献类型：
--
作者：
Davies GH;Molander GA
azaborine基序提供了一个独特的机会，通过在芳香支架中插入B-N单元来代替C=C键，创造出新的假芳香构建块，保留了类似的结构特征。先前合成1,3,2-苯并二氮杂硼核的方法是使用有机二氯化硼和硼酸作为硼前体。本文开发的转化完全利用了实验稳定的起始材料，包括有机三氟硼酸盐，在容易的反应条件下实现了更广泛的底物类似物阵列。此外，对这些化合物的物理、结构和电子性质进行了计算，以了解B-N取代对这些类似物的结构、芳香性和等构活力的影响。
The azaborine motif provides a unique opportunity to develop core isosteres by inserting B–N units in place of C=C bonds within aromatic scaffolds, creating new pseudoaromatic building blocks that retain comparable structural features. Previous synthetic routes to the 1,3,2-benzodiazaborole core have used organoboron dichlorides and boronic acids as the boron precursors. The transformation developed herein utilizes entirely bench stable starting materials, including organotrifluoroborates, enabling a wider array of substrate analogues under facile reaction conditions. Furthermore, physical, structural, and electronic properties of these compounds were explored computationally to understand the influence of the B–N replacement on the structure, aromaticity, and isosteric viability of these analogues.