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A kind of binuclear magnesium metal catalyst and its preparation method and application

A magnesium metal and catalyst technology, applied in the field of dual-nuclear magnesium metal catalyst and its preparation, can solve the problems of low selectivity, insufficient research and the like, and achieve the effects of simple preparation process, easy availability of raw materials and good application prospects

Active Publication Date: 2021-05-14
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Overall, the research is far from deep enough to break through the limitations of substrates and low selectivity to achieve general practical purposes.

Method used

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  • A kind of binuclear magnesium metal catalyst and its preparation method and application
  • A kind of binuclear magnesium metal catalyst and its preparation method and application
  • A kind of binuclear magnesium metal catalyst and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The preparation of embodiment 1 binuclear magnesium metal catalyst

[0017] Under the protection of inert gas and ice-water bath, di-n-butylmagnesium solution (3.00mL, 1.0M) was slowly added dropwise to the n-hexane solution of N-pyrromethene tert-butylamine ligand (0.451g, 3mmol). Complete, return to room temperature naturally, after continuing to stir for 2 hours, the resulting solution is cooled to zero degrees Celsius again with an ice-water bath, and o-methoxybenzaldehyde (0.408g, 3mmol) is added dropwise successively, and slowly returns to room temperature after the addition is completed. Stirring was continued for 7 hours, the reaction solution was concentrated in vacuo, extracted with ether, the extract was filtered and concentrated to a saturated state, left at room temperature for 1-2 days, and colorless transparent crystals were precipitated, which were binuclear magnesium metal catalysts (hereinafter referred to as catalysts), with a yield of 63 %.

[0018]...

Embodiment 2

[0021] (1) The preparation of the catalyst is the same as in Example 1.

[0022] (2) Catalytic benzaldehyde and o-bromobenzaldehyde cross-coupling Tishchenko reaction:

[0023]

[0024] At room temperature, benzaldehyde (0.212g, 2mmol) and o-bromobenzaldehyde (0.370g, 2mmol) were slowly added to the Schlenk reaction flask that catalyst (0.073g, 0.10mmol) was housed along the retort wall, and the temperature was controlled at 30 After stirring the reaction at ℃ for 4 hours, the reaction was terminated with 5 mL of water, extracted three times with ethyl acetate, the extract was concentrated in vacuo, and the crude product was separated by silica gel column chromatography to obtain the target product, a white solid, with a yield of 81%. 1 H NMR (600MHz, CDCl 3 ):δ=5.48(s,2H),7.24(t,1H),7.35(t,1H),7.48(m,2H),7.59(m,3H),8.13(d,J=6.4Hz,2H) ; 13 C (150.9MHz, CDCl 3 ): δ=66.2, 123.5, 127.6, 128.5, 129.7, 129.8, 129.9, 132.9, 133.2, 135.4, 166.2.

Embodiment 3

[0026] (1) The preparation of the catalyst is the same as in Example 1.

[0027] (2) Catalytic benzaldehyde and o-methoxybenzaldehyde cross-coupling Tishchenko reaction:

[0028]

[0029] At room temperature, benzaldehyde (0.212g, 2mmol) and o-methoxybenzaldehyde (0.272g, 2mmol) were slowly added to the Schlenk reaction flask containing the catalyst (0.073g, 0.10mmol) along the retort wall, and the temperature was controlled. After stirring the reaction at 30°C for 4 hours, the reaction was terminated with 5 mL of water, extracted three times with ethyl acetate, the extract was concentrated in vacuo, and the crude product was separated by silica gel column chromatography to obtain the target product, a white solid, with a yield of 79%. M.p.42-44℃. 1 H (600MHz, CDCl 3 ):δ=3.89(s,3H),5.45(s,2H),6.94-6.99(m,2H),7.33-7.36(m,1H),7.44-7.47(m,3H),7.58(t,1H ),8.11(d,2H); 13 C (150.9MHz, CDCl 3 ): δ=55.2, 61.7, 110.0, 120.2, 123.8, 127.9, 128.9, 129.0, 129.4, 129.7, 132.5, 157....

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Abstract

The invention provides a binuclear magnesium metal catalyst as well as its preparation method and application. Catalyst preparation method: under inert gas protection and ice-water bath conditions, first react with N-pyrromethene tert-butylamine ligand with equivalent di-n-butyl magnesium, react the gained solution at room temperature for 2-3 hours, and then add One times the amount of o-methoxybenzaldehyde was added dropwise, and after the reaction was completed, the reaction solution was concentrated in vacuo, extracted with ether, and the extract was filtered and concentrated to separate out colorless transparent crystals. The catalyst has high selectivity and catalytic activity for the cross-coupling Tishchenko reaction, and the preparation method is simple, the raw materials are easily obtained, the reaction conditions are mild, and the catalyst has good industrial application prospects.

Description

technical field [0001] The invention relates to an organometallic magnesium compound catalyst, in particular to a binuclear magnesium metal catalyst and a preparation method and application thereof. Background technique [0002] The synthesis of organic esters is an important transformation process in the fields of organic synthesis, pharmaceuticals and food flavor industries. Among them, the Tishchenko reaction has become one of the important reactions for the chemical synthesis of organic esters because it does not generate any by-products and has an atom economy of 100%. However, the Tishchenko reaction has never been a practical method for the synthesis of a large number of ester compounds. Its biggest limitation is that it can only be used to couple two molecules of the same aldehyde, and the resulting ester compounds are of a single type. [0003] Although, the Stephen J. Connon group has reported the highly selective cross-coupling Tishchenko reaction between differe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07F3/02C07C67/44C07C69/78C07C69/76C07C69/92
CPCB01J31/2217B01J2231/4288B01J2531/22C07C67/44C07F3/02C07C69/78C07C69/76C07C69/92
Inventor 郭志强王亚空魏学红
Owner SHANXI UNIV
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