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Supported cyclometalated iridium catalyst, preparation method thereof and application of supported cyclometalated iridium catalyst in dehydrogenation reaction of dihydroindolines compounds

A technology for catalyzing indoline and metal iridium, which is applied in the field of catalysis, can solve the problems of restricting the large-scale application of catalysts, difficulty in recycling, and difficulty in effective separation, and achieves the effects of short preparation cycle, high catalytic activity and good stability

Active Publication Date: 2015-12-16
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such cyclic metal iridium catalysts are expensive, difficult to effectively separate and difficult to recycle, etc., these problems largely limit the large-scale application of the catalyst

Method used

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  • Supported cyclometalated iridium catalyst, preparation method thereof and application of supported cyclometalated iridium catalyst in dehydrogenation reaction of dihydroindolines compounds
  • Supported cyclometalated iridium catalyst, preparation method thereof and application of supported cyclometalated iridium catalyst in dehydrogenation reaction of dihydroindolines compounds
  • Supported cyclometalated iridium catalyst, preparation method thereof and application of supported cyclometalated iridium catalyst in dehydrogenation reaction of dihydroindolines compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1. Synthesis of 4-methoxy-N-[1-(4-hydroxyphenyl)methylene]-aniline

[0032] With 2.72g p-hydroxyacetophenone, 2.95g p-methoxyaniline, 8.4g sodium bicarbonate, 12g activated Molecular sieves and 20mL of toluene were added to the flask in sequence, and heated to reflux for 72 hours under an argon atmosphere at a stirring speed of 1000r / min. Spin to dry, then recrystallize and purify with petroleum ether and ethyl acetate, then remove the mother liquor, and dry in vacuum at 40°C for 12 hours to obtain a light yellow solid 4-methoxy-N-[1-(4-hydroxyphenyl) Methyl]-aniline with a yield of 81.2%.

[0033] The Bruker600MHz superconducting Fourier digital nuclear magnetic resonance spectrometer of Bruker Company is used to measure the proton-nuclear magnetic spectrum of the light yellow solid obtained above, and its proton-nuclear magnetic spectrum is as follows figure 1 As shown, the NMR data are: 1 HNMR (600MHz, CDCl 3 )δ=7.83(d, J=8.4Hz, 2H), 6.90(d, J=8.4Hz, 2H), 6.81(d...

Embodiment 2

[0045] The use of the supported cyclic metal iridium catalyst obtained in Example 1 in catalyzing the dehydrogenation of indoline compounds, the specific method is as follows:

[0046] Add 20 mg of the supported cyclic metal iridium catalyst (the molar weight of the pyrene-labeled cyclic metal iridium complex is 0.005 mmol) into a 30 mL thick-walled pressure-resistant bottle, and then add 0.5 mmol of indoline compounds (see Table 1) and 3mL solvent (V 三氟乙醇 :V 水 =1:2), react at 100°C for 3 hours, cool to room temperature, transfer to a 10mL centrifuge tube with solvent, centrifuge at 10,000r / min for 3min, transfer the centrifugate, then add solvent to the centrifuge tube, shake the centrifuge tube Until the solid-liquid mixture is uniform, centrifuge at 10,000r / min for 3min, combine the centrifuged liquid twice, extract the reaction product with ethyl acetate, and use NMR analysis (internal standard is s-trimethoxybenzene) for dehydrogenation of indoline compounds The convers...

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Abstract

The invention discloses a supported cyclometalated iridium catalyst, a preparation method thereof and application of the supported cyclometalated iridium catalyst in dehydrogenation reaction of dihydroindolines compounds; the catalyst is loaded with a pyrene-loaded cyclometalated iridium complex by taking a multiwalled carbon nanotube as a carrier; in the cyclometalated iridium complex, an iridium atom is taken as a coordination center and 4-methoxy-n-[1-(4-hydroxyphenyl)]-phenylamine and pentamethylcyclo penta dience as ligands. The catalyst disclosed by the invention is simple in preparation method and short in preparation cycle and is capable of realizing the dehydrogenation reaction of the dihydroindolines compounds in green solvent (mixed solvent of water and trifluoroethanol); the reaction condition is mild, safe, green and efficient; the catalyst disclosed by the invention can be recovered through simple centrifugal separation, and the excellent catalytic performance of the catalyst is still kept after the catalyst is reused for multiple times.

Description

technical field [0001] The invention belongs to the technical field of catalysis, and in particular relates to a recyclable supported ring metal iridium catalyst, a preparation method of the catalyst and an application of the catalyst in catalyzing the dehydrogenation reaction of indoline compounds. Background technique [0002] The complex catalyst is a complex composed of a transition metal as the center. The transition metal atom at the center has electronic unsaturation of the d orbital, and interacts with different orbitals of the ligand to form a metal-ligand chemical bond. Complex catalysts have the advantages of high activity, good selectivity and mild reaction conditions. In organic catalytic reactions, complex catalysts also have the characteristics of a wide range of substrates and high conversion rates. For example, rhodium, iridium, ruthenium, and cobalt complexes catalyze the hydrogenation of monoolefins; Synthesis; palladium complexes catalyze coupling reacti...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07D209/08
CPCY02P20/50
Inventor 刘昭铁刘环王超陈建刚刘忠文肖建良
Owner SHAANXI NORMAL UNIV
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