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Nitrogen bridged bisphenol functionalized imidazole and ionic iron (III) complex thereof

A technology of imidazolium salt and imidazolium salt chemistry, applied in the direction of hydrocarbons, hydrocarbons, iron organic compounds, etc., can solve problems such as inconvenience of operation, and achieve the effects of eliminating interference, high yield and easy product

Inactive Publication Date: 2010-12-29
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this complex is oily at room temperature, which brings inconvenience to the operation

Method used

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  • Nitrogen bridged bisphenol functionalized imidazole and ionic iron (III) complex thereof
  • Nitrogen bridged bisphenol functionalized imidazole and ionic iron (III) complex thereof
  • Nitrogen bridged bisphenol functionalized imidazole and ionic iron (III) complex thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: N, N-di(3,5-di-tert-butyl-2 hydroxybenzyl)-2-hydroxyethylamine {[3,5-di-C(CH 3 ) 3 -2-OH-C 6 h 2 ]CH 2} 2 NCH 2 CH 2 Synthesis of OH

[0043] Add 2,4-di-tert-butylphenol (20g, 98.4mmol), formaldehyde (7.4mL, 98.4mmol) and 2-hydroxyethylamine (3mL, 49.2mmol) to methanol in turn, heat and reflux for six days, and the product is It was precipitated from the system, filtered with suction, washed with methanol, and the yield was 62%.

[0044] Carry out elemental analysis to product, test melting point, NMR analysis, the result is as follows:

[0045] Elemental analysis and melting point

[0046]

[0047] NMR data, 1 HNMR (CDCl 3 , δ, ppm) 8.40 (s, 2H, O-H), 7.18-7.21 (d, 2H, Ph-H), 6.86-6.91 (d, 2H, Ph-H), 3.84-3.90 (t, 2H, OCH 2 C), 3.74(s, 4H, PhCH 2 N), 2.70-2.75(t, 2H, NCH 2 C), 1.38(s, 18H, C(CH 3 ) 3 ), 1.25(s, 18H, C(CH 3 ) 3 ).

[0048] It was proved that the obtained compound was the target compound.

Embodiment 2

[0049] Example 2: N, N-di(3,5-di-tert-butyl-2 hydroxybenzyl)-2-chloroethylamine {[3,5-di-C(CH 3 ) 3 -2-OH-C 6 h 2 ]CH 2} 2 NCH 2 CH 2 Synthesis of Cl

[0050] (1) Dissolve N,N-bis(3,5-di-tert-butyl-2-hydroxybenzyl)-2-hydroxyethylamine (7.5g, 15mmol) in 100mL of anhydrous ether, Slowly add thionyl chloride (3.26mL, 41.25mmol) dropwise, after 30 minutes, slowly raise the temperature to 45°C, reflux for 3 hours, N,N-bis(3,5-di-tert-butyl-2-hydroxybenzyl Base)-2-chloroethylamine hydrochloride was precipitated from the system, filtered by suction, washed with ether, and the yield was 91%.

[0051] (2) Diethyl ether was added to N,N-bis(3,5-di-tert-butyl-2-hydroxybenzyl)-2-chloroethylamine hydrochloride, and then aqueous sodium bicarbonate was slowly added dropwise thereto. When the white solid in the solution disappears, stop the dropwise addition, wash three times with distilled water, and use 50 mL for one time, collect the ether layer, add an appropriate amount of anhyd...

Embodiment 3

[0057] Example three: Nitrogen-bridged bisphenol functionalized imidazolium salt {[(ArCH 2 ) 2 NCH 2 CH 2 NCHCHNR']CH}X, (X=Cl), R' is the synthesis of methyl

[0058] Under anhydrous and oxygen-free conditions, in an argon atmosphere, N,N-di(3,5-di-tert-butyl-2-hydroxybenzyl)-2-chloroethylamine (5g, 8mmol) and methylimidazole (0.8 mL, 9.6 mmol) was added to toluene, reacted at 115°C for 6 days, and the nitrogen-bridged bisphenol functionalized imidazolium salt was precipitated from the system, filtered by suction, washed with ethyl acetate, and the yield was 40%.

[0059] Carry out elemental analysis to product, test melting point, NMR analysis, the result is as follows:

[0060] Elemental analysis and melting point

[0061]

[0062] NMR data, 1 HNMR (CDCl 3 , δ, ppm) 10.65 (s, 1H, NCHN), 8.47 (s, 2H, O-H), 7.14-7.17 (d, 2H, Ph-H), 7.07 (s, 1H, NCHN), 6.98 (s, 1H , NCHC), 6.86-6.88 (d, 2H, Ph-H), 4.81-4.84 (t, 2H, NCH 2 C), 4.01(m, 1H, CH 3 ), 3.85(s, 4H, Ph CH ...

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Abstract

The invention belongs to the field of ligands and complexes, and in particular discloses a nitrogen bridged bisphenol functionalized imidazole and an ionic iron (III) complex thereof. The general formula of the nitrogen bridged bisphenol functionalized imidazole is ([(ArCH2)2NCH2CH2NCHCHNR']CH)X; and the general formula of the ionic iron (III) complex containing the imidazole is ([(ArCH2)2NCH2CH2NCHCHNR']CH)FeX'4, wherein Ar is 3,5-R-2-(OH)-C6H2, R is tertiary butyl, R' is one of methyl, isopropyl or benzyl, and X' is one of nitrogen or bromine. The invention also discloses application of thecomplexes to coupling reaction of aryl Grignard reagents and alkyl halohydrocarbon containing beta-H. The ionic iron (III) complex of the nitrogen bridged bisphenol functionalized imidazole has the characteristics of convenient and simple synthesis method, high yield, stable existence in air, and the like, and has high catalysis activity to the coupling reaction of the aryl Grignard reagents and the alkyl halohydrocarbon containing beta-H.

Description

technical field [0001] The invention belongs to the field of ligands and complexes, and in particular relates to a nitrogen-bridged bisphenol functionalized imidazolium salt and an ionic iron (III) complex thereof. Background technique [0002] The cross-coupling reaction catalyzed by transition metal complexes is one of the important methods for constructing carbon-carbon bonds in molecules (see: de Meijere, A.; Diederich, F., Eds.; Metal-Catalyzed Cross-Coupling Reactions, 2nd ed .; Wiley-VCH, Weinheim, 2004). Among them, palladium series or nickel series complexes are the most frequently used high-efficiency catalysts (referring to: Nicolaou, K.C.; Bulger, P.G.; Sarlah, D.Angew.Chem.Int.Ed.2005, 44,29,4442), however, they There are disadvantages such as high price or high toxicity. [0003] Iron-based catalysts have received increasing attention in the past decade due to their cheapness, low toxicity, and high efficiency (see: Plietker B., Ed.; Iron Catalysis in Organic...

Claims

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Application Information

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IPC IPC(8): C07D233/61C07F15/02B01J31/22C07C1/32C07C13/28C07C15/107
Inventor 孙宏枚闫春辉刘志宏沈琪
Owner SUZHOU UNIV
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