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Polyoxometalate catalyzed imine synthesis: Investigation of mechanistic pathways
Tetrahedron ( IF 2.1 ) Pub Date : 2020-05-07 , DOI: 10.1016/j.tet.2020.131245
Subhasis D. Adhikary , Debaprasad Mandal

The syntheses of imines by oxidative coupling of primary alcohols and amines were achieved by using 2 mol% polyoxometalate (POM) Na12[WZn3(H2O)2(ZnW9O34)2] (Zn–WZn3) catalyst in the presence of t-BuOK and di-oxygen with excellent conversion (up to 100%) and selectivity (up to 100%). Non-noble metal-based POM catalyst in the presence of base represents a new reaction protocol for the selective synthesis of imine from both aromatic and aliphatic primary amines with functional group tolerance. Control experiment shows the formation of di-oxygen bind Zn–WZn3 activated species. The electron-density of POM is mostly situated on the surface oxygen atoms of W–O–W bonds which can engage the alcoholic OH group and helps for the imine selectivity in the second step of imine synthesis.



中文翻译:

多金属氧酸盐催化的亚胺合成:机制途径的研究。

伯醇和胺的氧化偶合合成亚胺是通过在甲醇中使用2 mol%的多金属氧酸盐(POM)Na 12 [WZn 3(H 2 O)2(ZnW 9 O 342 ](Zn-WZn 3)催化剂来实现的。存在t -BuOK和双氧,具有出色的转化率(最高100%)和选择性(最高100%)。在碱存在下的基于非贵金属的POM催化剂代表了一种新的反应方案,用于从具有官能团耐受性的芳族和脂族伯胺选择性合成亚胺。对照实验表明形成双氧键的Zn–WZn 3活化物种。POM的电子密度主要位于W–O–W键的表面氧原子上,该键可以与醇性OH基团结合,并有助于亚胺合成的第二步中的亚胺选择性。

更新日期:2020-05-07
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