1,10-phenanthroline hydrate functionalized n-heterocyclic carbene and tetranuclear copper compound and preparation method for same

A technology of nitrogen heterocyclic carbene and o-phenanthroline, applied in the field of o-phenanthroline functionalized nitrogen heterocyclic carbene tetranuclear copper compound and its preparation, achieving the effects of convenient operation and control, high yield and easy preparation

Inactive Publication Date: 2014-06-11
WUHAN TEXTILE UNIV
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Problems solved by technology

However, in the published reports, there are still few studies on the "click" reaction catalyzed by copper carbene compounds, and they are limited to mononuclear copper carbene compounds, and the application of multinuclear metal copper carbene compounds in "click" reactions has not yet been seen. to report

Method used

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  • 1,10-phenanthroline hydrate functionalized n-heterocyclic carbene and tetranuclear copper compound and preparation method for same
  • 1,10-phenanthroline hydrate functionalized n-heterocyclic carbene and tetranuclear copper compound and preparation method for same
  • 1,10-phenanthroline hydrate functionalized n-heterocyclic carbene and tetranuclear copper compound and preparation method for same

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] a Under the protection of nitrogen at 1 standard atmospheric pressure, 2-iodo-o-phenanthroline (3.06g, 10mmol), imidazole (1.02g, 15mmol), cuprous oxide (2.16g, 15mmol), potassium carbonate (2.07g , 15mmol) and 45mLN, N'-dimethylformamide was added into a 100mL Schlenk reaction tube, reacted at 150°C for 15 hours, filtered after cooling to obtain a quality of 1.96g, and the yield was 80%. The molecular structural formula is:

[0027]

[0028] The calculated elemental analysis value of 2-imidazolyl-o-phenanthroline is C, 73.16; H, 4.09; N, 22.75; the measured elemental analysis value of 2-imidazolyl-o-phenanthroline is C, 73.30; H, 4.11; N, 22.45; The NMR spectrum of 2-imidazolyl-phenanthroline is: 1 H NMR (400MHz, CDCl 3 ): δ9.18(d, J=2.0Hz, 1H), 8.63(s, 1H), 8.35(d, J=8.4Hz, 1H), 8.24(d, J=8.0Hz, 1H), 7.99(s , 1H), 7.78(s, 2H), 7.68(d, J=8.0Hz, 2H), 7.66-7.62(m, 1H), 7.25(s, 1H). 13 C NMR (100MHz, CDCl 3 ): δ150.4, 147.9, 145.3, 145.2, 139.5, 136.2, 130.8, 129.4...

Embodiment 2

[0042] a Under the protection of nitrogen at 1 standard atmospheric pressure, 2-iodo-o-phenanthroline (3.06g, 10mmol), imidazole (1.02g, 15mmol), cuprous oxide (2.16g, 15mmol), potassium carbonate (2.07g , 15mmol) and 45mLN, N'-dimethylformamide was added into a 100mL Schlenk reaction tube, reacted at 150°C for 15 hours, filtered after cooling to obtain a quality of 1.96g, and the yield was 80%. The molecular structural formula is:

[0043]

[0044] The calculated elemental analysis value of 2-imidazolyl-o-phenanthroline is C, 73.16; H, 4.09; N, 22.75; the measured elemental analysis value of 2-imidazolyl-o-phenanthroline is C, 73.30; H, 4.11; N, 22.45; The NMR spectrum of 2-imidazolyl-phenanthroline is: 1 H NMR (400MHz, CDCl 3 ): δ9.18(d, J=2.0Hz, 1H), 8.63(s, 1H), 8.35(d, J=8.4Hz, 1H), 8.24(d, J=8.0Hz, 1H), 7.99(s , 1H), 7.78(s, 2H), 7.68(d, J=8.0Hz, 2H), 7.66-7.62(m, 1H), 7.25(s, 1H). 13 C NMR (100MHz, CDCl 3 ): δ150.4, 147.9, 145.3, 145.2, 139.5, 136.2, 130.8, 129.4...

Embodiment 3

[0058] a Under the protection of nitrogen at 1 standard atmospheric pressure, 2-iodo-o-phenanthroline (3.06g, 10mmol), imidazole (1.02g, 15mmol), cuprous oxide (2.16g, 15mmol), potassium carbonate (2.07g , 15mmol) and 45mLN, N'-dimethylformamide was added into a 100mL Schlenk reaction tube, reacted at 150°C for 15 hours, filtered after cooling to obtain a quality of 1.96g, and the yield was 80%. The molecular structural formula is:

[0059]

[0060] 2-imidazolyl-phenanthroline.

[0061] b. The compound (1.23g, 5mmol) and methylene bromide (3.5mL) obtained in step a were added into a 20mL Schlenk reaction tube, reacted at 100°C for 15 hours, collected by filtration after cooling to obtain imidazolium bromide, washed with 50mL of ether, and dried in vacuo. Dissolve the dried imidazolium bromide in 20 mL of methanol, and add 0.55 g of NaBF dropwise to the methanol solution 4 In the saturated aqueous solution of the solution, continue to stir for 60 minutes after the dropwise ...

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Abstract

The invention relates to a 1,10-phenanthroline hydrate functionalized N-heterocyclic carbene and tetranuclear copper compound and a preparation method for the same, which belong to the field of metal-organic chemistry. The 1,10-phenanthroline hydrate functionalized N-heterocyclic carbene and tetranuclear copper compound utilizes an N-heterocyclic carbene functionalized by 1,10-phenanthroline hydrate as a ligand, the molar ratio of the N-heterocyclic carbine to copper is 1:2, and a molecular structural formula of the compound is shown in the description, wherein X refers to one of PF6, BPh4 or BF4. The preparation method for the 1,10-phenanthroline hydrate functionalized N-heterocyclic carbene and tetranuclear copper compound is simple in preparation method, high in yield, stable in air and moisture, mild in 'click' reaction conditions for catalyzing trinitride and an alkynyl compound, high in catalyzing efficiency, environment-friendly, and can be widely applied to fine chemical engineering and pharmaceutical industry.

Description

technical field [0001] The invention relates to an o-phenanthroline functionalized nitrogen-heterocyclic carbene tetranuclear copper compound and a preparation method thereof, belonging to the field of metal organic chemistry. Background technique [0002] Click chemistry, also known as click chemistry, is a set of powerful, extremely reliable and highly selective chemistry first proposed by Nobel Prize winner Barry Sharpless (K.B.Sharpless) in 2001. The new method is another new technology that brings a major breakthrough to traditional organic synthetic chemistry after combinatorial chemistry. As one of them, the copper-catalyzed 1,3-dipolar cycloaddition reaction of azide and alkynyl compounds has good regioselectivity and high chemoselectivity, and can be carried out in aqueous media at room temperature or physiological temperature. advantages and has recently become the most widely used method in the fields of materials science, biology, and medicine. [0003] In rece...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08B01J31/22C07D249/06C07D401/06
Inventor 顾绍金徐卫林黄菁菁
Owner WUHAN TEXTILE UNIV
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