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Ionic type iron (III) complex with monophenol functionalization tetrahydroglyoxaline cations and preparation method and application thereof

A technology for imidazoline cationic and ionic, which is applied in the field of ionic iron complexes and their preparation, and achieves the effects of simple reaction system, favorable industrial application, and easy product

Active Publication Date: 2015-10-28
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been no reports of ionic iron(III) complexes containing monophenol-functionalized imidazolinium cations and their catalytic oxidative coupling reactions between aldehydes and secondary amides

Method used

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  • Ionic type iron (III) complex with monophenol functionalization tetrahydroglyoxaline cations and preparation method and application thereof
  • Ionic type iron (III) complex with monophenol functionalization tetrahydroglyoxaline cations and preparation method and application thereof
  • Ionic type iron (III) complex with monophenol functionalization tetrahydroglyoxaline cations and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment one: [(Ar 1 NCH 2 CH 2 NAr 2 )CH][FeX 4 ] (Ar 1 = 2,6-di-CH(CH 3 ) 2 -C 6 h 3 , Ar 2 = 2-(OH)-C 6 h 4 , X = Cl) for the synthesis of

[0038] Mix and dissolve 2,6-diisopropylaniline (10.0 ml, 48 mmol) and triethylamine (7.3 ml, 48 mmol) in dry tetrahydrofuran, slowly add oxalyl chloride monoethyl The ester (5.1 ml, 48 mmol) was stirred at room temperature for 5 hours after the addition was complete. After filtering, the filtrate was washed three times with dilute hydrochloric acid and saturated brine respectively, and the organic phase was dried with anhydrous sodium sulfate for 12 hours. The organic phase was concentrated to saturation, and 100 ml of n-hexane was added, a solid was precipitated, filtered, and dried to obtain a white solid ( N -(diisopropylphenyl)ethyl oxalate), the yield was 92%.

[0039] Dissolve the product in CDCl 3 Medium (about 0.4 mL), seal the tube, measure and characterize on a Unity Inova-400 NMR instrument at room...

Embodiment 2

[0055] Embodiment two: [(Ar 1 NCH 2 CH 2 NAr 2 )CH][FeX 4 ] (Ar 1 = 2,6-di-CH(CH 3 ) 2 -C 6 h 3 , Ar 2 = 2-(OH)-C 6 h 4 , X = Br) synthesis of

[0056] In turn [(Ar 1 NCH 2 CH 2 NAr 2 )CH]Cl (0.36 g, 1.0 mmol) and NaBr (0.62 g, 6.0 mmol) were added to a tetrahydrofuran solution of iron tribromide (0.30 g, 1.0 mmol), reacted at 45°C for 16 hours, and vacuum pumped The solvent was removed, washed with hexane, drained, extracted with tetrahydrofuran, and the supernatant liquid was transferred by centrifugation. Hexane was added to the supernatant liquid for recrystallization, and reddish-brown crystals were precipitated at room temperature, with a yield of 93%.

[0057] Carry out elemental analysis to product, the result is as follows:

[0058] Elemental analysis

[0059] C：（%） H：（%） N：（%） theoretical value 36.09 3.89 4.01 actual value 36.32 4.15 3.92

[0060] This complex [(Ar 1 NCH 2 CH 2 NAr 2 )CH][FeBr 4 ] exists in ...

Embodiment 3

[0062] Embodiment three: [(Ar 1 NCH 2 CH 2 NAr 2 )CH][FeX 4 ] (Ar 1 = 2,6-di-CH(CH 3 ) 2 -C 6 h 3 , Ar 2 = 3,5-di-C(CH 3 ) 3 -2-(OH)-C 6 h 2 , X = Cl) for the synthesis of

[0063] [(Ar 1 NCH 2 CH 2 NAr 2 )CH]Cl was synthesized referring to the steps of Example 1, using 3,5-di-tert-butyl-2-hydroxyaniline instead of 2-aminophenol.

[0064] Dissolve the product in CDCl 3 Medium (about 0.4 mL), seal the tube, measure and characterize on a Unity Inova-400 NMR instrument at room temperature: 1 H NMR (400 MHz, CDCl3, TMS): 8.27 (s, 1H), 7.47 (t, 1H), 7.36 (d, 1H), 7.31 (s, 1H), 7.29 (s, 1H), 6.96 (d, 1H), 4.92 (t, 2H), 4.48 (t, 2H), 3.51-3.40 (m, 2H), 1.44 (s, 9H), 1.37 (d, 6H), 1.30 (d, 15H)ppm.

[0065] Carry out elemental analysis to product, the result is as follows:

[0066] Elemental analysis

[0067] C：（%） H：（%） N：（%） theoretical value 73.93 9.20 5.95 actual value 73.72 8.96 5.88

[0068] Compound cationic part [(Ar ...

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Abstract

The invention discloses an ionic type iron (III) complex with monophenol functionalization tetrahydroglyoxaline cations and a preparation method and application thereof. The ionic type iron (III) complex with the monophenol functionalization tetrahydroglyoxaline cations is adopted as a catalyst to efficiently catalyze the oxidative coupling reaction of aldehyde and secondary amide to prepare imide for the first time, oxidative coupling of aromatic aldehyde, aliphatic aldehyde and the secondary amide can be efficiently catalyzed, the oxidative coupling reaction with aromatic heterocyclic aldehyde and large-steric-hindrance secondary amide as a substrate can be efficiently catalyzed, and catalytic activity and substrate applicability are superior to those in the prior art.

Description

technical field [0001] The invention relates to a metal complex and its application in the field of organic synthesis, in particular to an ionic iron (III) complex containing monophenolic functionalized imidazolinium cations and its preparation method and application. Background technique [0002] As an important structural unit, imide exists in many natural products, and is also an effective structural unit of many drugs, such as: aniracetam, penicillin, etc. Therefore, how to efficiently construct imide structures has received more and more attention (see: Y. J. Wang, C. Y. Chen, Z. Z. Huang, Chem. Eur. J. , 2013, 19, 1129). The coupling reaction of carboxylic acid derivatives and amides is one of the main traditional methods to construct imides, but this method is often limited by the instability and poor atom economy of carboxylic acid derivatives (such as: acid chlorides). (cf. C. A. G. N. Montalbetti, V. Falque, Tetrahedron , 2005, 61, 10827). As people pay more a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07C231/08C07C233/92C07D333/38C07D307/68C07C233/91C07D223/10C07F15/02B01J31/22
CPCB01J31/182B01J2231/4283B01J2531/842C07B43/06C07C231/08C07D223/10C07D307/68C07D333/38C07F15/02C07C233/92C07C233/91
Inventor 孙宏枚吴钰锋解存飞
Owner HUAWEI TEHCHNOLOGIES CO LTD
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