Fluorine-containing metal iridium complex as well as synthesis method and application thereof

A technology of metal iridium and complexes, which is applied in the field of fluorine-containing metal iridium complexes and their synthesis, can solve the problems of single iridium complexes, poor performance, unfavorable promotion, etc., and achieve low synthesis cost and easy operation. Simple, highly catalytic effect

Pending Publication Date: 2022-05-06
联碳新材料技术(杭州)有限公司 +1
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  • Summary
  • 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.
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 complex 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 promotion

Method used

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  • Fluorine-containing metal iridium complex as well as synthesis method and application thereof
  • Fluorine-containing metal iridium complex as well as synthesis method and application thereof
  • Fluorine-containing metal iridium complex as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Preparation of Intermediate I

[0034]

[0035] Under nitrogen protection, 0.58mol of 2-bromopyridine, 0.6mol of 2,4-difluorophenylboronic acid, 1.35mmol of Pd(dppf)Cl 2, 0.87mol of sodium carbonate was added to the three-necked flask, and then a mixed solution (1.2L) of 1,4-dioxane and water was added, wherein the volume ratio of 1,4-dioxane to water was 5 :1; then the mixed reaction solution was heated to 70°C and refluxed for 1h. After the reaction was completed, it was cooled to room temperature, and the solvent was distilled off 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 solvent was distilled off under reduced pressure to obtain a white solid intermediate I with a yield of 90.8%.

[0036] 2) Preparation of Intermediate II

[0037]

[0038] Under nitrogen protection, 28mmol o...

Embodiment 2

[0046] Example 2 The experimental process for preparing the iridium complex photocatalyst was repeated in Example 1, except that the 4,4'-bis(trifluoromethyl)-2,2'-bipyridine in step 3) was replaced by the same Molar amount of 5,5'-bis(trifluoromethyl)-2,2'-bipyridine, the rest of the operations were the same as in Example 1, and finally No. 2 novel iridium complex photocatalyst was obtained. The product was subjected to nuclear magnetic resonance detection, and the results were as follows: figure 2 shown.

Embodiment 3-5

[0052] The experimental process of embodiment 3-5 preparation iridium complex photocatalyst repeats embodiment 1, and difference only is that the proportioning of ethylene glycol methyl ether and water is different in step 2) (the ratio of ethylene glycol methyl ether and water mixed solution Total volume is constant 300mL), and all the other operations are with embodiment 1, and the intermediate II yield result that finally makes is as shown in table 2:

[0053] Table 2: Yields of products obtained with different ratios of ethylene glycol methyl ether and water

[0054]

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Abstract

The invention discloses a fluorine-containing metal iridium complex and a synthesis method and application thereof, the molecular formula of the fluorine-containing metal iridium complex is C34H20F16IrN4P, and the synthesis steps of the fluorine-containing metal iridium complex comprise four independent reactions: (1) taking an intermediate I formed by reaction of 2-bromopyridine and 2, 4-difluorophenylboronic acid as a ligand; (2) carrying out coordination reaction on the intermediate ligand I and an iridium compound to form an intermediate II; (3) reacting the intermediate II with 4, 4-bis (trifluoromethyl)-2, 2-dipyridyl or 5, 5-bis (trifluoromethyl)-2, 2-dipyridyl to obtain an intermediate III; and (4) finally, replacing chlorine in the intermediate III into PF6 by using an ammonium hexafluorophosphate aqueous solution, thereby completing the preparation. The metal iridium complex is applied to an alkylation reaction with tetrahydrofuran or N-Boc pyrrolidine as a substrate, a good alkylation reaction can be carried out under the heating condition under the condition that a blue light source is additionally arranged and weak organic base exists, the photocatalytic efficiency of the metal iridium complex is high, the yield of an addition product is high, and the metal iridium complex can be applied to the alkylation reaction of tetrahydrofuran or N-Boc pyrrolidine. The photocatalyst is an excellent photocatalyst worthy of popularization.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of transition metal complexes, in particular to a fluorine-containing metal iridium complex and its synthesis method and application. Background technique [0002] Alkylation reaction refers to the reaction of introducing alkyl (-R) into carbon, nitrogen, oxygen and other atoms in organic molecules. It is also an important step to introduce multifunctional alkylation groups into molecules to produce fine chemicals and synthetic building blocks. method. Photocatalytic reaction, with its advantages of mild reaction conditions, high efficiency, abundant visible light resources, and renewable, has revolutionized the field of organic alkylation reactions. [0003] Photocatalysts represented by iridium complexes have attracted widespread attention due to their excellent catalytic performance. There have been photocatalysts formed by related transition metals and fluorine-containing l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/22B01J31/18C07D207/08C07D307/12
CPCC07F15/0033B01J31/2295B01J31/1815B01J35/004C07D207/08C07D307/12B01J2531/827B01J2531/0241B01J2231/32
Inventor 马青余晓洪郝同川袁宇波胡燕君潘杰峰
Owner 联碳新材料技术(杭州)有限公司
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