Pd(Acac)2–Chiral Stabilizer–H2 Colloidal System in the Enantioselective Hydrogenation of N-Acetyl-α-Amidocinnamic Acid

IF 1.4 4区化学 Q4 CHEMISTRY, PHYSICAL

Colloid Journal Pub Date : 2024-09-05 DOI:10.1134/s1061933x24600532

L. O. Nindakova, V. O. Strakhov, N. M. Badyrova

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引用次数: 0

Abstract

It has been shown that the Pd(Acac)₂–mod–H₂ colloidal system, where mod denotes chiral stabilizers of molecular (8S,9R)-cinhonidine, (–)-Сin, and ionic (–)-Cin*HCl and (–)-Cin*2HCl types, exhibits catalytic activity in the asymmetric hydrogenation of N-acetyl-α-amidocinnamic acid (AACA) at room temperature and an H₂ pressure of 5 atm. The esterification reaction of the product, N-acetylphenylalanine (N-APhA), occurs in the presence of protonated forms of cinchonidine. The excess of the R-(–)-enantiomer of N-acetylphenylalanine is as large as 78% for the Pd(Acac)₂–(–)-Сin–H₂ system at (–)-Сin/Pd = 1.5, while the protonated forms of the quinine alkaloid show lower efficiency as modifiers of the catalytic system with respect to chiral induction. The X-ray diffraction analysis and high-resolution transmission electron microscopy have been employed to show the formation of palladium nanoparticles with average sizes of 5.3 ± 0.8 and 4.2 ± 0.5 nm for the Pd(Acac)₂–(–)-Cin–H₂ and Pd(Acac)₂–(–)-Сin *HCl–H₂ systems, respectively.

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Pd(Acac)2 手性稳定剂-H2 胶体系统在 N-乙酰基-α-脒基肉桂酸对映体选择性加氢反应中的应用

摘要研究表明，Pd(Acac)2-mod-H2 胶体系统（其中 mod 表示分子式 (8S,9R)-联苯胺、(-)-Сin 以及离子式 (-)-Cin*HCl 和 (-)-Cin*2HCl 类型的手性稳定剂）在室温和 5 atm 的 H2 压力下对 N-乙酰基-α-氨基肉桂酸 (AACA) 的不对称氢化具有催化活性。产物 N-乙酰基苯丙氨酸（N-APhA）的酯化反应是在质子化形式的辛可尼丁存在下发生的。在(-)-Сin/Pd = 1.5 时，Pd(Acac)2-(-)-Сin-H2 系统的 N-乙酰苯丙氨酸 R-(-)-对映体的过量率高达 78%，而奎宁生物碱的质子化形式作为手性诱导催化系统的调节剂，其效率较低。X 射线衍射分析和高分辨率透射电子显微镜显示，在 Pd(Acac)2-(-)-Cin-H2 和 Pd(Acac)2-(-)-Сin *HCl-H2 体系中分别形成了平均尺寸为 5.3 ± 0.8 nm 和 4.2 ± 0.5 nm 的钯纳米颗粒。

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来源期刊

Colloid Journal 化学-物理化学

CiteScore

2.20

自引率

18.20%

发文量

审稿时长

6-12 weeks

期刊介绍： Colloid Journal (Kolloidnyi Zhurnal) is the only journal in Russia that publishes the results of research in the area of chemical science dealing with the disperse state of matter and surface phenomena in disperse systems. The journal covers experimental and theoretical works on a great variety of colloid and surface phenomena: the structure and properties of interfaces; adsorption phenomena and structure of adsorption layers of surfactants; capillary phenomena; wetting films; wetting and spreading; and detergency. The formation of colloid systems, their molecular-kinetic and optical properties, surface forces, interaction of colloidal particles, stabilization, and criteria of stability loss of different disperse systems (lyosols and aerosols, suspensions, emulsions, foams, and micellar systems) are also topics of the journal. Colloid Journal also includes the phenomena of electro- and diffusiophoresis, electro- and thermoosmosis, and capillary and reverse osmosis, i.e., phenomena dealing with the existence of diffusion layers of molecules and ions in the vicinity of the interface.