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PD/ln heterometallic organic framework and its preparation method and application

An organic framework and heterogeneous metal technology, applied in the field of chemical functional materials and their preparation, can solve the problems of difficult recovery and reuse of palladium, waste, polluted products and the like

Active Publication Date: 2020-03-06
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, Pd(OAC) 2 , PdCl 2 Homogeneous catalysts have the advantages of high activity, high selectivity, and less side reactions, but their application is limited because the catalyst is difficult to separate, pollutes the product, and expensive palladium is difficult to recover and reuse, resulting in great waste.

Method used

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  • PD/ln heterometallic organic framework and its preparation method and application
  • PD/ln heterometallic organic framework and its preparation method and application
  • PD/ln heterometallic organic framework and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: Catalyst [H 3 O]n[SmPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[EuPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[TbPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[DyPd 2 [L] 2 Cl 4 ]n preparation

[0038] (1) 0.145 mmol 1,1'-bis(p-carboxybenzyl)-2,2'-bis-imidazole ligand, 0.09 mmol Sm(NO 3 ) 3 ·6H 2 O or Eu(NO 3 ) 3 ·6H 2 O or Tb(NO 3 ) 3 ·6H 2 O or Dy(NO 3 ) 3 ·6H 2 O, 0.15 mmol K 2 PdCl 4 , add 9mLH 2 O and 2mL of acetonitrile mixed solution, stirred at room temperature for 15min, a light yellow turbid solution appeared. The above solution was sealed in a reaction kettle with a 23mL polytetrafluoroethylene liner, kept at a temperature of 100°C for 72h, and cooled to room temperature. Yellow blocky crystals were obtained with a yield of 71%. The molecular formula is: [H 3 O]n[SmPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[EuPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[TbPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[DyPd 2 [L] 2 Cl 4 ] n.

[0039] (2) 0.145 mmol 1,1'-di(p-carboxybenzyl)-2,2'-bis-im...

Embodiment 2

[0048] Example 2: Pd / Ln heterometallic organic framework [H 3 O]n[SmPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[EuPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[TbPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[DyPd 2 [L] 2 Cl 4 Catalytic Activity of ]n on Suzuki C-C Coupling Reaction

[0049] (1) The yellow bulk crystal obtained in Example 1 [H 3 O]n[SmPd 2 [L] 2 Cl 4 ]n was used to verify its catalytic activity in the Suzuki C–C coupling reaction of aryl halides and phenylboronic acid. Specific operation method: 1 mmol aryl halide (chlorobenzene, bromobenzene or iodobenzene), 1.2 mmol phenylboronic acid, 2 mmol potassium carbonate and 0.4 mol% [H 3 O]n[SmPd 2 [L] 2 Cl 4 ]n into a round-bottomed flask, 6mL of deionized water as the reaction solvent, magnetically stirred at a temperature of 80 °C for 6 h, the solution after the reaction was extracted with ethyl acetate, and dried with anhydrous sodium sulfate, and then the organic solvent was removed Obtain final product, productive rate is measured...

Embodiment 3

[0061] Example 3: Pd / Ln heterometallic organic framework [H 3 O]n[SmPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[EuPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[TbPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[DyPd 2 [L] 2 Cl 4 ]n Catalytic activity for recycling in Suzuki C–C coupling reactions.

[0062] (1) Deionized water as the reaction solvent: After the Suzuki C-C coupling reaction in Example 2 (1)~(4) is completed, follow the instructions attached Figure 5 The method shown is to adjust the appropriate pH with the catalyst [H in the above reaction 3 O]n[SmPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[EuPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[TbPd 2 [L] 2 Cl 4 ]n or [H 3 O]n[DyPd 2 [L] 2 Cl 4 ]n separation, and put it into the Suzuki C-C coupling reaction of aryl halide and phenylboronic acid to verify its circular catalytic activity. Specific operation method: 1 mmol aryl halide (chlorobenzene, bromobenzene or iodobenzene), 1.2 mmol phenylboronic acid, 2 mmol potassium carbonate, and 0.4 mol% catalyst [H 3...

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Abstract

The Pd / Ln heterometallic organic framework and its preparation method and application relate to a chemical functional material and its preparation method and application. In the present invention, the Pd / Ln heterometallic organic framework is represented by Sm(NO 3 ) 3 ·6H 2 O or Eu(NO 3 ) 3 ·6H 2 O or Tb(NO 3 ) 3 ·6H 2 O or Dy(NO 3 ) 3 ·6H 2 O, Potassium tetrachloropalladate K 2 PdCl 4 , Azacyclic carboxylic acid 1,1'-bis(p-carboxybenzyl)-2,2'-bis-imidazole ligand is used as the reaction precursor, and is synthesized by solvothermal method. The molecular formula of the compound is [H 3 O]n[LnPd 2 [L] 2 Cl 4 ]n, where Ln represents Sm or Eu or Tb or Dy; L is 1,1'-bis(p-carboxybenzyl)-2,2'-biimidazole. The catalyst is novel in structure, simple in synthesis, high in yield and stable in air and water. The yield is greater than 99%. The catalyst can be reused by centrifugal separation in ethanol and water-ethanol solvent; it can be separated and recycled by adjusting the pH value in aqueous solution.

Description

technical field [0001] The invention relates to a chemical functional material and its preparation method and application, in particular to a Pd / Ln heterometallic organic framework, its preparation method and its application in catalytic Suzuki coupling reaction. Background technique [0002] The use of Suzuki coupling reaction to construct carbon-carbon bonds can transform simple reaction precursors into molecules with complex structures, which are widely used in the synthesis of various compounds such as medicines, pesticides and fine chemical products. [0003] Palladium-catalyzed carbon-carbon coupling reaction has the advantages of wide source of substrates, good compatibility of functional groups, mild reaction conditions and high yield, and is currently the most widely used catalyst. Among them, Pd(OAC) 2 , PdCl 2 Isohomogeneous catalysts have the advantages of high activity, high selectivity, and few side reactions, but their application is limited because the cata...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00B01J31/22C07C1/32C07C15/14C07C45/68C07C49/784
CPCB01J31/1691B01J2231/4205B01J2531/38B01J2531/824C07C1/321C07C45/68C08G83/008C07C15/14C07C49/784
Inventor 孙亚光崔蓝心由立新丁茯熊刚王淑菊
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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