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Dinuclear half-sandwich iridium complex containing bisimine ligand and preparation method and application thereof

A technology of iridium complex and bis-imine, applied in the field of synthetic chemistry, can solve problems such as product yield decline, and achieve the effects of less by-products, high thermal stability and high yield

Active Publication Date: 2019-04-05
SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many methods for synthesizing aldehydes, such as alcohols are oxidized to prepare aldehydes, acids are reduced to prepare aldehydes, and olefins are oxidized to prepare aldehydes (this method usually requires a strong acidic environment, which requires high equipment and produces a large amount of acidic wastewater. ) and so on, but there are few studies on the direct oxidation of halogenated hydrocarbons as raw materials to prepare aldehydes. Usually, they are first hydrolyzed into alcohols, and then further oxidized into corresponding aldehydes. Every additional step in the synthesis process will generate additional waste water Waste residue, and the yield of the final product will also be reduced

Method used

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  • Dinuclear half-sandwich iridium complex containing bisimine ligand and preparation method and application thereof
  • Dinuclear half-sandwich iridium complex containing bisimine ligand and preparation method and application thereof
  • Dinuclear half-sandwich iridium complex containing bisimine ligand and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of the binuclear semi-sandwich iridium complex containing double imine ligand

[0023]

[0024] At -78°C, n-BuLi (1.6M) in n-hexane (1.0 mL, 1.6 mmol) was added dropwise to the pyrrole-cyclobis-imine ligand C 10 h 10 N 4 (119.0mg, 0.64mmol) in tetrahydrofuran solution, continue to stir for 50 minutes after the dropwise addition, slowly rise to room temperature and continue to react for 60 minutes, then add pentamethylcyclopentadienyl iridium chloride dimer [Cp * IrCl 2 ] 2 (460.0mg, 0.58mmol), continued to react at room temperature for 4 hours; after the reaction was over, it was left to stand and filtered, and the solvent was drained under reduced pressure, and the crude product obtained was separated by column chromatography (petroleum ether / dichloromethane (v / v )=6:1) to obtain orange-red target product C 30 h 38 Cl 2 Ir 2 N 4 (437.0 mg, 83% yield). Its crystal structure is shown in figure 1 shown. Single crystal culture met...

Embodiment 2

[0027] Example 2: Oxidation of halogenated hydrocarbons to aldehydes catalyzed by dinuclear semi-sandwich iridium complexes containing bis-imine ligands

[0028]

[0029] The catalyst prepared in Example 1 was used to catalyze the oxidation reaction of halogenated hydrocarbons: to bromoethane (1mmol, 109mg) and DMSO solution containing binuclear semi-sandwich iridium complex (0.001mmol, 0.9mg) was added, open reaction, reaction The temperature is 30°C, and the reaction time is 270 minutes. After the reaction, the reaction solution is washed with water, extracted and concentrated. The crude product is separated by silica gel column chromatography and dried until the quality remains unchanged to obtain the corresponding aldehyde compound C 2 h 4 O (41 mg, 93% yield), elemental analysis: C 54.53, H 9.15 (theoretical); C 54.43, H 9.19 (actual).

Embodiment 3

[0030] Example 3: Oxidation of halogenated hydrocarbons to aldehydes catalyzed by dinuclear semi-sandwich iridium complexes containing bis-imine ligands

[0031]

[0032] Adopt the catalyst prepared in Example 1 to catalyze the oxidation reaction of halogenated hydrocarbons: add the DMSO solution containing binuclear half-sandwich iridium complex (0.001mmol, 0.9mg) to chloropropane (1mmol, 80mg), open reaction, reaction temperature 50°C, the reaction time is 300 minutes. After the reaction, the reaction solution is washed with water, extracted and concentrated. The crude product is separated by silica gel column chromatography and dried until the quality remains unchanged to obtain the corresponding aldehyde compound C 3 h 6 O (55 mg, 95% yield), elemental analysis: C 62.04, H 10.41 (theoretical); C 62.03, H 10.53 (actual).

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Abstract

The invention belongs to the technical field of synthetic chemistry and relates to a dinuclear half-sandwich iridium complex containing bisimine ligand and a preparation method and application thereof. Pentamethylcyclopentadienyl iridium chloride dimer [(C5Me5)IrCl2]2 is used as a raw material subjected to reaction with pyrrole ring-containing bisimine ligand under alkaline conditions to prepare the finished N,N-coordinated dinuclear half-sandwich iridium complex. The synthetic process herein is simple and green and has good selectivity and high yield; the dinuclear half-sandwich iridium complex herein has stable physio-chemical properties and thermal stability and the like and shows efficient catalytic activity in the reaction where halogenated hydrocarbons are oxidized into correspondingaldehydes.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, and specifically relates to a dinuclear semi-sandwich iridium complex containing a bis-imine ligand, a preparation method and an application thereof. Background technique [0002] Aldehydes are an important class of organic compounds, which are widely used in many fields such as wood processing industry, textile industry, medical and health care, oil extraction, leather tanning and so on. With the continuous development and growth of various industries in our country, the demand for aldehydes and their derivatives will also increase. Moreover, aldehyde compounds are also an important class of organic synthesis intermediates, and aldehyde groups can be converted into various compounds such as carboxylic acids, alcohols, and amines through reactions. At present, there are many methods for synthesizing aldehydes, such as alcohols are oxidized to prepare aldehydes, acids are reduced to p...

Claims

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Application Information

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IPC IPC(8): C07F17/02B01J31/22C07C47/06C07C45/32C07C47/02C07C205/44C07C201/12C07C47/198C07C47/54
CPCB01J31/2295B01J2231/70B01J2531/0225B01J2531/0252B01J2531/827C07B2200/13C07C45/32C07C201/12C07F17/02C07C47/06C07C47/02C07C47/198C07C47/54C07C205/44
Inventor 姚子健靳永旭云雪静高永红邓维
Owner SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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