First Tetradentate Diamidophosphite Based on [5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrinato]zinc: Synthesis, Spectral Features, Coordination, and Application in Asymmetric Pd-Catalyzed Reactions

IF 1 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Macroheterocycles Pub Date : 2021-01-01 DOI:10.6060/mhc200918g

I. S. Mikhel, K. Gavrilov, S. Zheglov, Ivan M. Novikov, K. P. Birin, A. Chernyadyev, V. Tyurin

引用次数: 0

Abstract

The synthesis of the tetradentate diamidophosphite ( L ) containing four 1,3,2-diazaphospholidine rings and a porphyrin moiety, its characterization and application in asymmetric Pd-catalyzed reactions are reported. The best results (up to 63 % ee) were obtained for the Pd-catalyzed allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethylmalonate. The complex L [Ru(p-cymene)Cl 2 ] 4 was synthesized in situ and characterized by spectroscopic data. The structure of the compounds obtained is discussed based on 1 H, 13 C, 13 C DEPT, 31 P, 1 H- 13 C HSQC, 1 H- 13 C HMBC, 1 H- 1 H COSY, 1 H- 1 H ROESY NMR spectroscopy, as well as UV-Vis and fluorescence spectroscopy.

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基于[5,10,15,20-四(4-羟基苯基)卟啉]锌的第一四齿二磷酯:合成、光谱特征、配位及其在不对称pd催化反应中的应用

报道了含4个1,3,2-重氮膦环和1个卟啉基团的四齿二磷酯(L)的合成、表征及其在不对称pd催化反应中的应用。pd催化(E)-1,3-二苯丙烯酯乙酸酯与二甲基丙二酸酯的烯丙基烷基化反应获得了最佳结果(ee达63%)。原位合成了配合物L [Ru(对伞花烃)Cl 2] 4，并用光谱数据对其进行了表征。用1 H、13 C、13 C DEPT、31 P、1 H- 13 C HSQC、1 H- 13 C HMBC、1 H- 1 H COSY、1 H- 1 H ROESY核磁共振波谱以及紫外可见光谱和荧光光谱对所得化合物的结构进行了讨论。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Macroheterocycles CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

2.30

自引率

21.40%

发文量

期刊介绍： The journal is a forum for the specialists investigating macroheterocyclic compounds. It publishes original experimental and theoretical works (full papers and short communications) and reviews on synthesis, structural characterization, physical and coordination chemistry as well as practical application of macroheterocycles.