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A Nitrogen Activation and Conversion Process Promoted by Divalent Rare Earth Iodides

A technology of diiodide and rare earth, applied in the fields of organic chemistry, hydrazone preparation, etc., can solve the problem that nitrogen molecules cannot be converted, etc.

Inactive Publication Date: 2019-01-15
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention solves the problem that nitrogen molecules coordinated with rare earth metals cannot be further transformed for a long time, and enables nitrogen to become the nitrogen source in the synthesis of organic nitrogen-containing compounds under mild conditions

Method used

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  • A Nitrogen Activation and Conversion Process Promoted by Divalent Rare Earth Iodides

Examples

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Effect test

Embodiment 1

[0021] Example 1, put dysprosium iodide (1.0 mmol) and tetrahydrofuran (15 ml) into a glass reaction bottle, react at -25 °C for 24 h under a nitrogen atmosphere of 0.1 MPa, then add 1 M HCl (3 ml), Stir for 30 minutes, then add benzaldehyde (2.0 mmol). After stirring at 70°C for 12 hours, 1M NaOH was added for neutralization. The reaction solution was extracted with ether, the solvent was removed, and the residue was purified by silica gel column chromatography to obtain 46 mg of benzaldehyde azine with a yield of 88%.

[0022] 1 H NMR (CDCl 3 , 400 MHz): 8.67(s, 2H), 7.84-7.86(m, 4H), 7.44-7.46(m, 6H). 13 C NMR (CDCl 3 , 100MHz): 162.06, 131.20, 128.79, 128.56. GC-MS: m / z=208 [M+].

Embodiment 2

[0023] Example 2, put dysprosium iodide (1.0 mmol) and 1,4-dioxane (15 ml) into a glass reaction bottle, react at -78 °C for 24 h under a nitrogen atmosphere of 0.5 MPa, and then add l M HCl (3 ml), stirred for 30 minutes, followed by the addition of acetophenone (1.0 mmol). After stirring at 70°C for 12 hours, 1M NaOH was added for neutralization. The reaction solution was extracted with ether, the solvent was removed, and the residue was purified by silica gel column chromatography to obtain 25 mg of acetophenone azine with a yield of 42%.

[0024] 1 H NMR (CDCl 3 , 400 MHz): 7.90-7.92(m, 4H), 7.42-7.44(m, 6H), 2.32(s, 6H). GC-MS: m / z=236 [M+].

Embodiment 3

[0025] Example 3, put dysprosium iodide (1.0 mmol) and diethyl ether (15 ml) into a glass reaction bottle, react at -40 °C for 24 h under a nitrogen atmosphere of 0.1 MPa, and then add 1 M H 2 SO 4 (2.5 ml), stirred for 30 minutes, followed by the addition of p-methoxybenzaldehyde (2.0 mmol). After stirring at 70°C for 12 hours, 1M NaOH was added for neutralization. The reaction solution was extracted with ether, the solvent was removed, and the residue was purified by silica gel column chromatography to obtain 41 mg of p-methoxybenzaldehyde azine with a yield of 61%.

[0026] 1 H NMR (CDCl 3 , 400 MHz): 8.61(S, 2H), 7.77(d, 4H, J = 8.67 Hz), 6.95(d,4H, J = 8.66 Hz), 3.86(s, 6H). 13 C NMR (CDCl 3 , 100MHz): 160.88, 130.12, 131.20, 55.39. GC-MS: m / z=268 [M+].

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for activating and converting nitrogen through a divalent rare earth compound. A divalent rare earth diodide is used as a reducing agent, a solvent is added in, the mixture reacts with nitrogen, then a hydrogen source is added in, and then the mixture reacts with an aldehyde or ketone compound to obtain an azine or pyridazine compound. According to the method, the nitrogen is activated and converted into the organic compound containing nitrogen on the mild condition. Compared with a classical ammonia synthesis path, strict reaction conditions such as high temperature, high pressure and ammonia oxidation are avoided, and the method is of great significance in developing the new technology of nitrogen molecule activation and broadening the application range of rare earth metal in organic synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for activating and converting nitrogen through divalent rare earth compounds. Background technique [0002] Nitrogen (N) is not only one of the important elements (14-18%) of protein, but also the basic raw material for artificial synthesis and modification of various functional materials, which plays a vital role in life activities and human survival and development. Existing industrial nitrogen fixation method: through artificially designed catalysts, nitrogen reacts with hydrogen at high temperature and high pressure (350~550 ℃, 150~350 atm), which is the most important method in industry (Angew. Chem. Int .Ed . 2008, 47, 3524.). However, this method has harsh conditions, very high equipment requirements, and consumes a lot of energy and non-renewable resources. [0003] Evans et al. have reported that a series of low-priced rare ear...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D237/30C07C251/88C07C249/16
CPCC07C249/16C07D237/30C07C251/88
Inventor 周锡庚王岩朱振宇
Owner FUDAN UNIV
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