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N-heterocyclic carbene palladium complex with ptycene structure and application thereof

A technology of complexes and pterenes, which is applied in the direction of palladium organic compounds, platinum group organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of no reactivity and achieve broad commercialization prospects and high Reaction yield, enhance the effect of industrialization process

Active Publication Date: 2020-05-08
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The Suzuki-Miyaura coupling reaction between heterocyclic chlorides and heterocyclic boronic acids under air conditions (J.Org.Chem.2017, 82, 10898-10911) has been reported, but its disadvantage is that for nitrogen-containing heterocyclic boronic acids Low-activity heterocyclic boronic acids such as pyrimidine, carbazole, quinoline, and isoxazole have almost no reactivity, so these catalysts still have many limitations in application

Method used

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  • N-heterocyclic carbene palladium complex with ptycene structure and application thereof
  • N-heterocyclic carbene palladium complex with ptycene structure and application thereof
  • N-heterocyclic carbene palladium complex with ptycene structure and application thereof

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Experimental program
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Effect test

Embodiment 1

[0034] The chemical synthesis route of N-heterocyclic carbene palladium complex with pterene structure is shown below.

[0035] (1) Synthesis of Pterenone Compound A

[0036]

[0037] Under the protection of nitrogen, anthracene (1.78 g, 10.0 mmol) and vinylene carbonate (8.60 g, 100.0 mmol) were successively added into a 100 mL thick-walled bottle, and the mixture was refluxed at 180° C. for 8 h. After the reaction, the reaction solution was cooled to room temperature, methanol was added to the reaction solution and stirred. After a large amount of solid precipitated out of the reaction system, it was suction filtered. The solid was repeatedly washed with methanol and dried in vacuo to obtain white compound A with a yield of 82%.

[0038] (2) Synthesis of Pterene Diols Compound B

[0039]

[0040] Compound A (2.11g, 8.0mmol), 1,4-dioxane (90mL) and 4N NaOH solution (5ml) were added to a 250ml check flask, and the reaction was refluxed at 100°C for 2h. Cool to room t...

Embodiment 2

[0088] Example 2 N-heterocyclic carbene palladium complexes with pterene structure catalyzed Suzuki-Miyaura coupling reaction

[0089] The experimental steps for testing the catalytic activity of the N-heterocyclic carbene palladium complex with a pterene structure for the Suzuki-Miyaura coupling reaction are as follows:

[0090] Set up a control group experiment, 2-thiophene boronic acid (1.0mmol), 2-chloropyridine (1.0mmol) as substrate, mixed with sodium carbonate (2mmol), and tetrahydrofuran and water (1:3v / v, 4ml) as solvent Added into parallel reaction tubes, C1-C3, D1, E1 (0.1 mol% of the substrate) were respectively used as catalysts and added into parallel tubes. Then react in air at 80°C for 4h. After the reaction, the parallel reaction tubes were cooled to room temperature, and extracted by adding ethyl acetate and water for 2-3 times. The organic layer was dried with anhydrous sodium sulfate, the remaining reaction solution was evaporated by rotary evaporation, t...

Embodiment 3

[0100] Due to the high reactivity of thiophene boronic acid, the results in the comparison experiment can not fully reflect the high activity of the pterene skeleton structure catalyst, so a series of nitrogen-containing heterocyclic chlorides (1.0mmol) with lower activity, nitrogen-containing heterocyclic Cycloboronic acid (1.0mmol) was used as a substrate, mixed with sodium carbonate (2mmol), and added to parallel reaction tubes with tetrahydrofuran and water (1:3v / v, 4ml) as a solvent, and the N-heterocycle disclosed by the present invention Carbene palladium complexes C1-C3 (0.5 mol% of substrate) as catalysts were added to parallel tubes. Then react in air at 80°C for 0.5h. After the reaction, the parallel reaction tubes were cooled to room temperature, and extracted by adding ethyl acetate and water for 2-3 times. The organic layer was dried with anhydrous sodium sulfate, and the remaining reaction solution was evaporated by rotary evaporation. The separated product was...

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Abstract

The invention relates to an N-heterocyclic carbene palladium complex with a ptycene structure. A three-dimensional skeleton is provided, so that the steric hindrance can be increased and a carbon-carbon double bond located between C11 and C12 of vinylidene anthracene in the skeleton structure prevents arylamine from overturning around a carbon-nitrogen bond. Therefore, beta-hydrogen elimination and catalyst deactivation are inhibited, and the reaction activity of the catalyst is greatly improved. The Suzuki-Miyaura coupling reaction between the nitrogen-containing heterocyclic chloro compoundserving as a substrate and the low-activity nitrogen-containing heterocyclic boric acid is realized, the reaction can undergo under mild conditions of air and water, and meanwhile, a relatively high reaction yield is ensured.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to an N-heterocyclic carbene palladium complex with a pterene structure and an application thereof. Background technique [0002] The construction of aromatic heterocycles through reactions between heterocycles and heterocycles and other structural units has always been an important and challenging part in the field of C-C, C-N cross-coupling reactions. The Suzuki–Miyaura coupling reaction can effectively construct C-C and C-N bonds, so it is widely used in the synthesis fields of natural products, agrochemicals, pharmaceutical active ingredients, fine chemicals and engineering materials. In the past decades, the transition metal-catalyzed Suzuki-Miyaura coupling reaction has been considered as the most efficient and reliable method. However, most of the catalysts in the reaction use phosphorus-containing ligands, so these catalysts cause serious environmental pollution,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/22C07D401/04C07D403/04C07D215/18
CPCC07F15/006B01J31/2273C07D401/04C07D403/04C07D215/18B01J2231/4211B01J2231/4227B01J2531/824
Inventor 黄菊
Owner GUANGDONG PHARMA UNIV
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