SiCl4-catalyzed/PR3-mediated β-C(sp3)−H functionalization of nitrones to α,β-unsaturated imines and aromatic heterocycles
作者:De-Ping Zhu、Bao-Hua Xu、Yi-Ran Du、Suo-Jiang Zhang
DOI:10.1016/j.tet.2018.03.038
日期:2018.5
A novel method of SiCl4-catalyzed/PR3-mediated β-C(sp3)−H functionalization of nitrones with aldehydes/ketones to α,β-unsaturated imines was developed. The synthesis of α,β-unsaturated imines mainly invovles deoxygenation and aldol condensation, each proceeding under a cooperation effect between Lewis acid and Lewis base. In addition, both the acidity and hydrolytic stability of the weak SiCl4 were
开发了一种新的SiCl 4催化/ PR 3介导的醛-酮将β- C(sp 3)-H官能化为α,β-不饱和亚胺的新方法。α,β-不饱和亚胺的合成主要涉及脱氧和醛醇缩合,它们各自在路易斯酸和路易斯碱之间的协同作用下进行。另外,认为弱硅氯化硅4的酸度和水解稳定性都可以通过与由PR 3引起的硝酮脱氧而产生的氧化膦(R = Et)或磷酸三酰胺(R = NMe 2)来增强。。在六元硝酮的情况下,所得的α,β-不饱和亚胺中的[1,3]-氢化物移位导致芳构化,从而导致3,5-二烷基吡啶。