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Alpha-diimine nickel metal organic ligand, porous organic polymer and application of porous organic polymer

A metal-organic and nickel diimide technology, which is applied in the direction of nickel-organic compounds, preparation of organic compounds, organic compound/hydride/coordination complex catalysts, etc., can solve the problems of high cost and low catalytic activity of palladium catalysts, etc. Short reaction time, excellent stability, and improved catalytic effect

Active Publication Date: 2019-09-13
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inventors of the present disclosure understand that the palladium catalyst has the disadvantages of low catalytic activity and high cost.

Method used

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  • Alpha-diimine nickel metal organic ligand, porous organic polymer and application of porous organic polymer
  • Alpha-diimine nickel metal organic ligand, porous organic polymer and application of porous organic polymer
  • Alpha-diimine nickel metal organic ligand, porous organic polymer and application of porous organic polymer

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Embodiment approach

[0044] A typical embodiment of the present disclosure provides α-diimine nickel metal organic ligand, whose chemical structural formula is:

[0045]

[0046] Another embodiment of the present disclosure provides a method for preparing the above-mentioned organic ligand, which is obtained by ketone-amine condensation reaction of 2,6-diisopropyl-p-iodoaniline and 2,3-butanedione.

[0047] In one or more examples of this embodiment, the ketone-amine condensation reaction condition is: the reaction is carried out at room temperature with formic acid as a catalyst. The room temperature mentioned in the present disclosure refers to the indoor temperature, which is generally 15-30°C.

[0048] The third embodiment of the present disclosure provides monomers for preparing porous organic polymers, the chemical structural formula of which is:

[0049]

[0050] The fourth embodiment of the present disclosure provides a method for preparing the above-mentioned monomer, and anhydrous...

Embodiment 1

[0070] Example 1: Preparation of α-diimine nickel metal organic ligand (A).

[0071] (1) 2,6-Diisopropylaniline (2.54g, 14.3mmol) and I 2 (4 g, 15.7 mmol) of the mixture was charged to a 50 mL round bottom flask. Then 10 mL of cyclohexane and 4 mL of saturated Na 2 CO 3 solution. After stirring at room temperature for 12 h, diluted with EtOAc (20 mL), saturated Na 2 S 2 o 3 (3 x 40 mL) wash. with anhydrous MgSO 4 The combined organic layer was dried. The crude product was purified by column chromatography (petroleum ether / EtOAc=10 / 1) to obtain 4-iodo-2,6-diisopropylaniline as a black liquid (3.90 g, yield 96%).

[0072] (2) Add 4-iodo-2,6-diisopropylaniline (14mmol, 3.7g) into a 50mL round bottom flask, and then add ditributanedione (7mmol, 0.611mL) into the round bottom flask , add 0.5mL formic acid as catalyst, use 20mL ethanol as solvent, stir at room temperature for 5h, after the reaction, filter with Buchner funnel, wash with a small amount of ethanol, and dry t...

Embodiment 2

[0080] Example 2: Preparation of monomer (B) of porous organic polymer.

[0081] A (1.1mmol, 0.722g) and DME (NiBr 2 ) (1mmol, 0.308g) was mixed in 50mL of anhydrous dichloromethane and placed in a 100mL Schlenk flask. After stirring at room temperature under nitrogen for 2 days, the reaction was filtered through a pad of celite. The resulting solid was further washed with anhydrous ether and dried in vacuo to obtain B as a brick red solid (0.59g, 68.0%), characterized by the following structure: Figure 3-4 shown.

[0082] The synthetic route of B is as follows:

[0083]

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Abstract

The disclosure provides an alpha-diimine nickel metal organic ligand, a porous organic polymer and application of the porous organic polymer. The porous organic polymer has a chemical structural formula as shown in the description. The porous organic polymer can be applied to preparation of a catalyst for catalyzing a Suzuki coupling reaction, and the catalyst has high catalytic activity, low cost, low usage amount and repeated use.

Description

technical field [0001] The disclosure belongs to the technical field of catalyst preparation, and relates to α-diimine nickel metal-organic ligands, porous organic polymers and applications thereof. Background technique [0002] The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art. [0003] Suzuki reaction, also known as Suzuki coupling reaction, Suzuki-Miyaura reaction (Suzuki-Miyaura reaction), is an organic coupling reaction in which aryl or alkenyl boronic acid or boron is catalyzed by a zero-valent palladium complex Esters cross-couple with chlorine, bromine, iodoarenes or alkenes. The Suzuki reaction was first reported by Akira Suzuki in 1979. It is widely used in organic synthesis, has strong substrate adaptability and functional group tolerance, and is often used to synthesize derivatives of polyenes, styrene and biphenyl, thus applying In the synthesis of many natural products an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/08C07C249/02B01J31/16B01J31/18C07B37/04C07C1/32C07C17/263C07C41/30C07C45/68C07C67/343C07C201/12C07F15/04C07C253/30C07C15/14C07C205/06C07C49/784C07C43/205C07C255/50C07C22/08C07C69/78C07C205/12C08G61/12
CPCC07C251/08C07F15/045B01J31/1691B01J31/1805C08G61/123C07C1/321C07C201/12C07C45/68C07C41/30C07C253/30C07C17/263C07C67/343C07B37/04C08G2261/12C08G2261/415C08G2261/323C08G2261/312B01J2231/4227C07C15/14C07C205/06C07C49/784C07C43/205C07C255/50C07C22/08C07C69/78C07C205/12
Inventor 鞠晶晶董育斌董英
Owner SHANDONG NORMAL UNIV
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