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Fluorine-containing transition metal complex as well as preparation method and application thereof

A technology for transition metals and complexes, which is applied in the synthesis and application of transition metal complexes, can solve the problems of complex methods, high cost, consumption of manpower and material resources, etc., and achieves the effects of high catalytic activity, low synthesis cost and simple operation.

Pending Publication Date: 2022-07-22
联碳新材料技术(杭州)有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the types of related iridium complexes are relatively single, and the performance is not very good, and each catalyst can only catalyze the alkylation addition of one or several related compounds.
The synthesis of most iridium catalysts needs to be processed through columns and other methods, which is not only complicated but also consumes a lot of manpower and material resources
For example, the DuPont research team synthesized organometallic iridium complexes under the catalysis of a small amount of silver trifluoromethanesulfonate (Grushin V.V., et al., Chem. Commun., 2001, 1494-1495), but the iridium complexes synthesized by this method The substance can only be the same as the ligand, and because the ligand is used as the reaction raw material and solvent at the same time, the cost is very high, which is not conducive to popularization

Method used

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  • Fluorine-containing transition metal complex as well as preparation method and application thereof
  • Fluorine-containing transition metal complex as well as preparation method and application thereof
  • Fluorine-containing transition metal complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1) Preparation of Intermediate I

[0027]

[0028] Under nitrogen protection, 0.58 mol of 2-bromo-5-fluoropyridine, 0.6 mol of 2,4-difluorobenzeneboronic acid, 1.35 mmol of Pd(dppf)Cl 2 , 0.87mol of sodium carbonate was added to the three-necked flask, and then the mixed solution (1.2L) of 1,4-dioxane and water was added, wherein the volume ratio of 1,4-dioxane and water was 5 : 1; then the mixed reaction solution was heated to 70 °C and refluxed for 1 h. After the reaction was completed, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The obtained solid was separated and extracted with water and MTBE, and the organic phase was washed with saturated brine and water successively, dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a white solid Intermediate I for subsequent use, Intermediate I Yield 95.1%.

[0029] 2) Preparation of In...

Embodiment 2

[0039] Example 2 The experimental procedure for preparing the fluorine-containing transition metal iridium complex was repeated in Example 1, except that the 2,2'-bipyridine in step 3) was replaced with an equivalent molar amount of 5,5'-bis(tripyridine) Fluoromethyl)-2,2'-bipyridine, and other operations are the same as those in Example 1, and finally No. 2 novel fluorine-containing transition metal iridium complex is obtained. The product was tested by nuclear magnetic resonance, and the results were as follows figure 2 shown.

Embodiment 3-5

[0045] Example 3-5 The experimental procedure for preparing fluorine-containing transition metal iridium complexes was repeated in Example 1, except that the proportions of ethylene glycol methyl ether and water in step 2) were different (ethylene glycol methyl ether and water were mixed The total volume of the liquid is constant 300mL), and all the other operations are the same as in Example 1, and the specific results of the yield that finally obtain intermediate II are shown in Table 2

[0046] Table 2: Yields of products obtained from ethylene glycol methyl ether and water in different proportions

[0047]

[0048]

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Abstract

The invention discloses a fluorine-containing transition metal complex and a preparation method and application thereof.The catalyst is a complex C34H18F18IrN4P generated from a fluorine-containing ligand and an iridium metal precursor in situ, and the preparation method comprises the steps that an intermediate I formed by 2-bromine-5-fluoropyridine and 2, 4-difluorophenylboronic acid serves as a ligand and is subjected to a coordination reaction with an iridium compound to form an intermediate II, and then the intermediate II and 2, 4-difluorophenylboronic acid are subjected to a reaction to form the fluorine-containing transition metal complex. The preparation method comprises the following steps: reacting 5, 5-bis (trifluoromethyl)-2, 2-dipyridyl or 5, 5-bis (trifluoromethyl)-2, 2-dipyridyl to obtain an intermediate III, and finally replacing chlorine with PF6 by using an ammonium hexafluorophosphate aqueous solution to obtain a final product. The prepared photocatalyst is applied to alkylation reaction of tetrahydrofuran or N-Boc pyrrolidine, and the alkylation reaction can be carried out under the heating condition under the condition of weak organic alkali and an external visible light source; the metal iridium compound serving as the photocatalyst for the addition reaction is high in efficiency, the yield of alkylated products can reach about 70%, and the metal iridium compound is a photocatalyst worthy of popularization.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of transition metal complexes, and particularly relates to a fluorine-containing transition metal complex, a preparation method and application thereof. Background technique [0002] Visible light-catalyzed organic synthesis will become one of the must-go strategies for organic synthesis. Visible light resources in my country are abundant and renewable, and the reaction conditions of visible light catalysis are mild and efficient. Visible light photoredox catalysis has great advantages over traditional synthesis methods in many aspects. The concept of visible light catalysis has been proposed for more than 100 years. Among them, the photocatalytic reaction represented by the photocatalytic a-alkylation reaction has aroused great interest and has developed rapidly in recent years. A key technology in synthesis. [0003] Photocatalysts represented by iridium complexes have attrac...

Claims

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Application Information

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IPC IPC(8): C07F15/00B01J31/22C07D307/12C07D207/08
CPCC07F15/0033B01J31/2295C07D307/12C07D207/08B01J2531/827B01J2231/32B01J35/39
Inventor 马青余晓洪郝同川齐孝林易玲潘杰峰
Owner 联碳新材料技术(杭州)有限公司
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