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首页> 外文期刊>RSC Advances >Anionic phenoxy-amido rare-earth complexes as efficient catalysts for amidation of aldehydes with amines
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Anionic phenoxy-amido rare-earth complexes as efficient catalysts for amidation of aldehydes with amines

机译：阴离子苯氧基-酰胺基稀土配合物作为醛与胺酰胺化的有效催化剂

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摘要

A series of anionic organo-rare-earth amido complexes stabilized by dianionic phenoxy-amido ligands were prepared and their catalytic behavior for amidation reactions of aldehydes with amines was elucidated. Amine elimination reaction of Ln[N(SiMe3)(2)](3)(mu-Cl)Li(THF)(3) with an equimolar of lithium aminophenoxy {[HNO]Li-1(THF)}(2), which was prepared by the reaction of [HNOH](1){[HNOH](1) = N-p-fluoro-phenyl(2-hydroxy-3,5-di-tert-butyl) benzylamine} with one equivalent of n-BuLi in tetrahydrofuran (THF) in situ, gave the anionic phenoxy-amido rare earth amido complexes [NO](1)(2)Ln[N(SiMe3)(2)][Li(THF)](2) [Ln = Y (1), Yb (2), Sm (3), Nd (4)] in high isolated yields. Similar reactions of Ln[N(SiMe3)(2)](3)(mu-Cl)Li(THF)(3) with {[HNO]Li-2(THF)}(2), and {[HNO]Li-3(THF)}(2) in THF gave the anionic rare-earth amides [NO](2)(2)Ln [N(SiMe3)(2)][Li(THF)](2) [Ln = Sm (5), Nd (6)] and [NO](3)(2)Ln[N(SiMe3)(2)][Li(THF)](2) [Ln = Sm (7), Nd (8)] {[HNOH](2) = N-p-chloro-phenyl(2-hydroxy-3,5-di-tert-butyl) benzylamine; [HNOH](3) = N-p-bromophenyl (2-hydroxy-3,5-di-tert-butyl) benzylamine}, respectively. All of these complexes were fully characterized. X-ray structural determination revealed that these complexes are isostructural, and have solvated monomeric structures. Each of the rare-earth ions is coordinated by two phenoxy-amido ligands and one N(SiMe3)(2) group, and the coordination geometry can be described as a distorted trigonal bipyramid. Each of the lithium atoms is surrounded by one aryloxo group, one amido group and one THF molecule, and the coordination geometry can be described as a trigonal plane. The catalytic behavior of these rare-earth amides for the amidation reaction of aldehyde with amine was elucidated. It was found that these complexes are efficient catalysts for this transformation to produce amides in good to excellent yields under mild reaction conditions, and in some cases, diacylamide compounds can be prepared conveniently.
机译：制备了一系列由双阴离子苯氧基-酰胺基配体稳定的阴离子有机稀土酰胺配合物，并阐明了它们对醛与胺酰胺化反应的催化作用。 Ln [N（SiMe3）（2）]（3）（mu-Cl）Li（THF）（3）与等摩尔的氨基苯氧基锂{[HNO] Li-1（THF）}（2）的胺消除反应，它是通过[HNOH]（1）{[HNOH]（1）= Np-氟苯基（2-羟基-3,5-二叔丁基）苄胺}与一当量的n-BuLi反应制得的原位在四氢呋喃（THF）中，得到阴离子苯氧基-酰胺基稀土酰胺基络合物[NO]（1）（2）Ln [N（SiMe3）（2）] [Li（THF）]（2）[Ln = Y （1），Yb（2），Sm（3），Nd（4）]高分离产率。 Ln [N（SiMe3）（2）]（3）（mu-Cl）Li（THF）（3）与{[HNO] Li-2（THF）}（2）和{[HNO] Li THF中的-3（THF）}（2）得到阴离子稀土酰胺[NO]（2）（2）Ln [N（SiMe3）（2）] [Li（THF）]（2）[Ln = Sm （5），Nd（6）]和[NO]（3）（2）Ln [N（SiMe3）（2）] [Li（THF）]（2）[Ln = Sm（7），Nd（8） ] {[HNOH]（2）＝ Np-氯-苯基（2-羟基-3,5-二叔丁基）苄胺; [HNOH]（3）分别为N-对溴苯基（2-羟基-3,5-二叔丁基）苄胺}。所有这些复合物均已充分表征。 X射线结构测定表明这些络合物是同构的，并且具有溶剂化的单体结构。每个稀土离子均由两个苯氧基-酰胺基配体和一个N（SiMe3）（2）基团配位，并且配位几何可描述为扭曲的三角双锥体。每个锂原子被一个芳氧基，一个酰胺基和一个THF分子包围，并且配位几何可描述为一个三角平面。阐明了这些稀土酰胺对醛与胺的酰胺化反应的催化行为。已发现这些络合物是在温和的反应条件下用于该转化以良好至优异产率产生酰胺的有效催化剂，并且在某些情况下，可以方便地制备二酰基酰胺化合物。

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