School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Kerala 695551, India.
Org Biomol Chem. 2020 May 6;18(17):3354-3359. doi: 10.1039/d0ob00419g.
1,1,2-Triarylethanes embedded with an azaarene unit were prepared in a single step at ambient temperature via the sodium hexamethyldisilazide mediated 1,6-conjugate addition of unactivated alkylazaarenes on para-quinone methides (p-QMs). The extent of this methodology was investigated with a wide range of p-QMs and alkylazaarenes, and the respective products were obtained in moderate to excellent yields. The regioselective 1,6-conjugate addition of the trialkylazaarene precursor on para-quinone methide was also presented. Besides, we showcased the direct synthesis of the 1,1,2-triarylethane derivative from aldehyde via the in situ generation of para-quinone methide.
1,1,2-三芳基乙烷嵌入一个氮杂芳烃单元，通过未活化的烷基氮杂芳烃在对醌甲醚（p-QM）上的钠六甲基二硅氮烷介导的 1,6-共轭加成，在环境温度下一步制备。该方法的范围广泛，包括各种 p-QM 和烷基氮杂芳烃，相应的产物以中等至优异的产率获得。还提出了三烷基氮杂芳烃前体在对醌甲醚上的区域选择性 1,6-共轭加成。此外，我们展示了通过对醌甲醚的原位生成，从醛直接合成 1,1,2-三芳基乙烷衍生物。
