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Rare-earth metal organic compound, as well as preparation method and application thereof

A technology of organic compounds and rare earth metals, which is applied in the field of metal-organic compound preparation, to achieve the effects of simple and easy-to-operate reaction process, wide applicability, and high yield

Inactive Publication Date: 2013-06-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] But, in prior art, do not see the report of the rare earth organometallic compound that takes Salalen as ligand

Method used

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  • Rare-earth metal organic compound, as well as preparation method and application thereof
  • Rare-earth metal organic compound, as well as preparation method and application thereof
  • Rare-earth metal organic compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Preparation of SalalenH 2 (R 1 = Bu t , R 2 = CPhMe 2 )

[0057] Add 4.68 g (20 mmol) of 3,5-di-tert-butyl salicylaldehyde into a two-neck flask with a stirring bar, add methanol to dissolve, add two drops of glacial acetic acid, and then add N-methylethylenediamine 1.8 mL (20 mmol), stirred for half an hour, then added 6.60 g (20 mmol) of 2,4-di(a,a-dimethylphenylmethyl)phenol, 0.9 g (30 mmol) of paraformaldehyde ), reacted at 70° C. for 12 hours, a large amount of yellow solids were precipitated, filtered by suction, washed the filter cake with methanol, and dried by suction, the yield was 71%. Elemental analysis: C, 81.78; H, 8.74; N, 4.66. High resolution mass spectrum C 43 h 57 N 2 o 2 Theoretical value: 633.4420; Measured value: 633.4407. NMR: 1 H NMR (400 MHz, DCCl 3 , 25 °C): δ 8.12 (s, 1H, N=CHAr), 7.37 (s, 1H, ArH), 7.20-7.06 (m, 12H, ArH), 6.72 (s, 1H, ArH), 3.61 (s , 2H, ArCH 2 N), 3.45 (s, 2H, NCH 2 ), 2.63 (s, 2H, NCH 2 ), 2.2...

Embodiment 2

[0058] Embodiment two: [(Salalen)Y(OCH 2 Ph)] 2 (R 1 =R 2 = Bu t )

[0059] Will Cp 3 A solution of Y(THF) (2.81 mmol) in tetrahydrofuran was added to SalalenH 2 (1.44 g, 2.81 mmol) in tetrahydrofuran solution, stirred at 25°C for about 1 hour, and the system turned into a light yellow transparent solution. Benzyl alcohol (0.29 mL, 2.81 mmol) was then added by syringe, and the reaction was stirred for about 8 hours at 25°C. Remove tetrahydrofuran, add 10 ml of toluene to extract twice, centrifuge to remove a little precipitate, transfer the supernatant, concentrate, room temperature overnight, 1.58 g of colorless crystals are precipitated, and the yield is 80%. Elemental analysis: C, 68.79; H, 8.77; N, 3.68; Y, 12.84. C 80 h 114 N 4 o 6 Y 2 Theoretical values: C, 68.36; H, 8.17; N, 3.99; Y, 12.65); infrared spectrum (KBr pellet, cm -1): 2950 s, 2900 s, 2860 s, 1620 s, 1530 m, 1470 s, 1440 s, 1410 s, 1360 m, 1310 m, 1230 m, 1200 m, 1160 m, 1010 m, 879 w, 839 w...

Embodiment 3

[0060] Embodiment three: [(Salalen)Sm(OCH 2 Ph)] 2 (R 1 =R 2 = Bu t )

[0061] Will Cp 3 A solution of Sm(THF) (2.40 mmol) in tetrahydrofuran was added to SalalenH 2 (1.23 g, 2.40 mmol) in tetrahydrofuran solution, stirred at 25°C for about 1 hour, and the system turned into a yellow transparent solution. Benzyl alcohol (0.25 mL, 2.40 mmol) was then added by syringe, and the reaction was stirred for about 8 hours at 25°C. Remove tetrahydrofuran, add 10 ml of hexane to extract twice, centrifuge to remove a little precipitate, transfer the supernatant, concentrate, room temperature overnight, 1.39 g of yellow crystals are precipitated, and the yield is 76%. Elemental analysis: C, 62.55; H, 7.69; N, 3.81; Sm, 19.54. C 80 h 114 N 4 o 6 SM 2 Theoretical values: C, 62.86; H, 7.52; N, 3.67; Sm, 19.67); Infrared spectrum (KBr pellet, cm -1 ) 2950 s, 2901 s, 2860 s, 1620 s, 1530 m, 1470 s, 1440 s, 1410 s, 1360 m, 1310 m, 1230 m, 1200 m, 1160 m, 1010 m, 879 w, 841 w, ...

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Abstract

The invention discloses a rare-earth metal organic compound, as well as a preparation method and application thereof. The rare-earth metal organic compound is expressed by the following chemical general formula of [(Salalen)Ln(OR)]2, in the formula, Ln is rare-earth metal; R is aryl or alkyl; R<1> and R<2> are respectively selected from one of H, CH3, Bu<t> and CPhMe2; and R<3> is selected from CH3 or Ph. The Salalen-type rare-earth metal organic compound disclosed by the invention is simple in synthesis, convenient to separate and purify, clear in structure, high in yield, high in activity when used as a catalyst for catalyzing the reaction between phosphite ester and aldehyde or ketone, and wide in substrate universality.

Description

technical field [0001] The invention relates to the field of preparation of metal organic compounds, in particular to a rare earth metal organic compound and its preparation and application. Background technique [0002] Asymmetric synthesis is a basic method to obtain optically pure compounds. Asymmetric synthesis methods include substrate-induced asymmetric synthesis and catalyst-induced asymmetric synthesis, and the most attractive one is chiral catalyst-induced asymmetric synthesis. It has become a hot spot in the field of organic synthetic chemistry research. Among them, chiral diamine Schiff base metal complexes with C1 symmetry, such as (1R,2R)-N,N-3,5-disubstituted salicylaldehyde-1,2-cyclohexanediamine and its derivatives The synthesis of compounds and their research in the field of asymmetric catalysis are very active. This kind of chiral Schiff base metal complexes are called Salen-type, Salan-type and Salalen-type catalysts (see: Ziegler J. E., Du G., Fanwick P....

Claims

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Application Information

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IPC IPC(8): C07F5/00C07F9/40B01J31/22
Inventor 姚英明聂昆
Owner SUZHOU UNIV