Complex containing 2-aminopyridine tetradentate ligand and application thereof

A technology of tetradentate ligands and metal complexes, which is applied in the preparation of hydroxyl compounds, organic compound/hydride/coordination complex catalysts, compounds containing elements of Group 8/9/10/18 of the periodic table, etc., can Solve the problems of low catalytic efficiency and high cost of catalyst use, and achieve the effects of convenient use, strong stability and high activity

Inactive Publication Date: 2014-04-09
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2011, Takasago Corporation of Japan reported the hydrogenation reduction of esters by PNP-Ru(Ru-MACHO) complex d [3] , the complex is simple and easy to obtain, but the catalytic efficiency is still not high
[0005] The above introduction basically includes the latest progress of ester hydrogena

Method used

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  • Complex containing 2-aminopyridine tetradentate ligand and application thereof
  • Complex containing 2-aminopyridine tetradentate ligand and application thereof
  • Complex containing 2-aminopyridine tetradentate ligand and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0081] Specific examples of some of the preferred tetradentate ligands L(I) to L(XIII) of the present invention are given below:

[0082]

[0083]

[0084] The metal M in the general formula (1) will be described. The metal M can be exemplified by the metal elements of the sixth, seventh, and eight subgroups. The metal elements of the sixth subgroup are Fe, Ru, and Os, and the metal Ru is more preferable.

[0085] The metal compound as the starting material for preparing the metal complex in the present invention is not particularly limited, and for example, FeCl 2 , FeBr 2 , FeCl 3 , FeBr 3 , RuCl 3 Hydrate, RuBr 3 Hydrate, RuI 3 Inorganic compounds such as hydrate, RuCl 2 (DMSO) 4 ,, [Ru(cod)Cl 2 ] n , [Ru(nbd)Cl 2 ] n , (Cod)Ru(2-methallyl) 2 , [Ru(benzene)Cl 2 ] 2 , [Ru(p-cymene)Cl 2 ] 2 , [Ru(mesitylene)Cl 2 ] 2 , [Ru(hexamethylbenzene)Cl 2 ] 2 , RuCl 2 (PPh 3 ) 3 , RuHCl(PPh 3 ) 3 , RuH(OAc)(PPh 3 ) 3 , RuH 2 (PPh 3 ) 4 Wait. In the above example, DMSO is dimethyl sulfoxide, c...

Example Embodiment

[0103] Example 1

[0104] The preparation of methyl 6-formyl 2-picolinate, the synthesis reaction formula and steps are as follows:

[0105]

[0106] Put 11.5g (50mmol) of ethyl 2,6-pyridinedicarboxylate in a 500ml dry flask, add 400ml of methanol, place the reaction flask in an ice bath at 0℃, and slowly add 1.9g (50mmol) of NaBH 4 , Continue the reaction for 1h at this temperature, and slowly add 1g NaBH again 4 , React at 0℃ for 1h, add 0.5g NaBH again 4 , React for 1h at 0℃, add 200ml saturated sodium bicarbonate solution, stir at 0℃ for 30min, spin dry methanol, the obtained aqueous phase is extracted with chloroform (100ml×5), the organic phase is dried with anhydrous sodium sulfate, spin-dried to obtain a white solid . Dissolve the white solid in 300ml of dichloromethane, slowly add 12.9g (60mmol) of PCC (pyridinium chlorochromate) at room temperature, stir at room temperature for 4h, filter the resulting black solution with diatomaceous earth, and wash with dichloromethane....

Example Embodiment

[0107] Example 2

[0108] The preparation of methyl 6-dimethoxymethyl-2-picolinate, the synthesis reaction formula and steps are as follows:

[0109]

[0110] Put 2.4g (14.5mmol) of methyl 6-formylpyridine-2-carboxylate in a 250ml dry flask. Under nitrogen atmosphere, add 50ml of anhydrous methanol and 50ml of trimethylorthoformate in sequence. Heat to 70℃ and stir for 4h. After the reaction is detected by TLC, cool to room temperature, spin-dry to about 5ml of liquid remaining, add 50ml of water, extract the product three times with ethyl acetate, the obtained organic phase is dried, spin-dried, and the crude product is purified by column chromatography to obtain 2.9 g White solid, yield 90%.

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Abstract

The invention relates to a metal complex MXY(L) and a method for hydrogenation reduction preparation of alcohol from carbonyl compounds containing ketone, esters and the like by using the complex as a catalyst. In the MXY(L), M is selected from metals Fe, Ru, Os, Co, Rh, Ir and other transition metals; X and Y may be the same or different anionic ligands; L is a tetradentate ligand containing -NH- pyridyl and two heteroatoms. The complex disclosed by the invention has the advantages of being high in catalytic activity, strong in stability and the like.

Description

technical field [0001] The invention relates to a complex containing 2-aminopyridyl tetradentate ligand and a method for preparing alcohol by hydrogenating and reducing esters or lactones by using the complex as a catalyst, belonging to the field of organic synthesis. Background technique [0002] The reduction of ester or lactone compounds to alcohol compounds is a very important method in chemical synthesis, and in natural compounds, the number of ester compounds is huge, and natural fatty acids are reduced to fatty alcohols after esterification, which has been industrialized for more than seven years. ten years. Traditional ester reduction generally utilizes high temperature and high pressure (100-300atmH 2 , 200-300℃), heterogeneous catalytic system, high energy consumption, or using metal reducing reagents such as sodium borohydride or lithium aluminum hydride, it needs to consume equivalent or several times the equivalent of the metal reducing reagent of the substrate...

Claims

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Application Information

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IPC IPC(8): C07F9/58C07D213/36C07D213/38C07D401/14C07F15/00B01J31/24C07C29/149C07C33/22C07C31/08C07C31/20
Inventor 张绪穆谭雪锋
Owner WUHAN UNIV
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