Chiral pyridine biimidazole ligand transition metal complex catalyst and preparation method thereof

A technology of pyridine bis-imidazole and transition metal, which is applied in the field of chiral pyridine bis-imidazole ligand transition metal complex catalyst and its preparation, can solve the problems of expensive ligands and difficult synthesis, and achieve cheap and easy-to-obtain raw materials. The effect of simple synthesis operation and simple preparation method

Inactive Publication Date: 2016-08-17
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no reports about other metal complexes catalyzing this type of reaction, and the ligands used by Hall’s and Yun’s groups are expensive and difficult to synthesize.

Method used

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  • Chiral pyridine biimidazole ligand transition metal complex catalyst and preparation method thereof
  • Chiral pyridine biimidazole ligand transition metal complex catalyst and preparation method thereof
  • Chiral pyridine biimidazole ligand transition metal complex catalyst and preparation method thereof

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Effect test

Embodiment 1

[0036] Embodiment 1: prepare chiral pyridine bis-imidazole ligand-iron complex 1a of the present invention, its structural formula is:

[0037]

[0038] In the glove box, the FeCl 2 (126.8 mg, 1.0 mmol, 1.0 equiv) and THF (50 mL) were added to a 100 mL schlenk tube, and then a THF solution (10 mL) of chiral pyridine bis-imidazole ligand (1.04 g, 2.0 mmol, 2.0 equiv) was slowly added The above solution was added dropwise, and at the moment of addition, the color of the reaction solution rapidly changed to purple-black, and a purple-black solid was precipitated. After the reaction was stirred at room temperature for 24 h, it was filtered, washed with THF and ether, and the solvent was drained to obtain a purple-black powder (1.02 g, 87%). Then put the above powder (15 mg) into a sample bottle with a volume of 4 mL, dissolve it in DMSO (1 mL), transfer the above sample bottle to a sample bottle with a volume of 18 mL containing ether solvent, and the ether solvent cannot cov...

Embodiment 2

[0039] Embodiment 2: Preparation of chiral pyridine bis-imidazole ligand-iron complex [(NNN) of the present invention 2 Fe] 2+ FeCl 4 2- (complex 1b), its structural formula is:

[0040]

[0041] In the glove box, the FeCl 2 (126.8 mg, 1.0 mmol, 1.0 equiv) and THF (50 mL) were added to a 100 mL schlenk tube, and then a THF solution (10 mL) of chiral pyridine bis-imidazole ligand (575.7 mg, 1.0 mmol, 1.0 equiv) was slowly added The above solution was added dropwise, and at the moment of addition, the color of the reaction solution rapidly changed to purple-black, and a purple-black solid was precipitated. After the reaction was stirred at room temperature for 24 h, it was filtered, washed with THF and ether, and the solvent was drained to obtain a purple-black powder (583.1 mg, 83%). Anal. Calcd for C 78 h 74 Cl 4 Fe 2 N 10 : C, 66.68; H, 5.31; N, 9.97. Found: C, 67.06; H, 5.68; N, 10.26.

Embodiment 3

[0042] Embodiment 3: Preparation of chiral pyridine bis-imidazole ligand-iron complex [(NNN) of the present invention 2 Fe] 2+ Cl 2 2- (complex 1c), its structural formula is:

[0043]

[0044] In the glove box, the FeCl 2 (126.8 mg, 1.0 mmol, 1.0 equiv) and THF (50 mL) were added to a 100 mL schlenk tube, and then a THF solution (10 mL) of chiral pyridine bis-imidazole ligand (1.11 g, 2.0 mmol, 2.0 equiv) was slowly added The above solution was added dropwise, the color of the reaction solution rapidly changed to purple-black, and a purple-black solid was precipitated. After the reaction was stirred at room temperature for 24 h, it was filtered, washed with THF and ether, and the solvent was drained to obtain a purple-black powder (1.00 g, 81%). Anal. Calcd for C 70 h 56 Cl 4 FeN 10 : C, 68.08; H, 4.57; N, 11.54. Found: C, 68.53; H, 4.91; N, 11.70.

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Abstract

The invention relates to a chiral pyridine biimidazole ligand transition metal complex catalyst and a preparation method thereof. The general structure of the compound is shown in the description, wherein M represents transition metal, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8> and R<9> represent hydrogen atoms or alkane groups of C1-C30 or aryl groups of C6-C30, X represents a halogen atom or halogenated metal salt ion, the asterisk place is racemization or chirality, and when the asterisk place is chirality, the asterisk place represents an R configuration or S configuration. An applied chiral pyridine biimidazole ligand can change the electronic property and steric hindrance of the ligand through functional group modification, and as a catalyst precursor, asymmetric hydroboration of alkenyl borane has medium catalytic activity and stereoselectivity. According to the chiral pyridine biimidazole ligand transition metal complex catalyst and the preparation method thereof, the preparation method is simple, the raw materials are cheap and easy to obtain, environmental friendliness is achieved, the reaction condition is mild, the yield is high, and synthetic operation is easy and convenient.

Description

technical field [0001] The invention relates to a chiral pyridine bis-imidazole ligand transition metal complex catalyst and a preparation method thereof. Background technique [0002] Due to the advantages of high efficiency and low consumption, transition metal catalysts have attracted widespread attention of scientific researchers. However, in the field of homogeneous catalysis, noble metal catalytic systems are still dominant. Precious metals have limited reserves, are expensive, and are toxic to heavy metals. In contrast, cheap metals are abundant and environmentally friendly. Therefore, it is of great practical value to develop new cheap metal catalysts to replace noble metal catalysts in transition metal catalyzed reactions. In the past ten years, the use of cheap metal catalysts in homogeneous catalytic reactions has been widely developed. [0003] Ligands play a vital role in transition metal-catalyzed reactions, and the efficiency and selectivity of reactions c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07F15/02C07F15/06C07B53/00C07F5/02
CPCB01J31/1815B01J2231/323C07B53/00C07B2200/07C07F5/025C07F15/025C07F15/065
Inventor 彭思瀚龚和贵黄正张雷
Owner SHANGHAI UNIV
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