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Iridium complex with photocatalytic performance as well as preparation method and application thereof

An iridium complex, photocatalytic technology, applied in indium organic compounds, platinum group organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem of single iridium complexes, not very good performance, Unfavorable promotion and other problems, to achieve the effect of low synthesis cost, simple operation and high catalytic activity

Pending Publication Date: 2022-05-13
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.
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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  • Iridium complex with photocatalytic performance as well as preparation method and application thereof
  • Iridium complex with photocatalytic performance as well as preparation method and application thereof
  • Iridium complex with photocatalytic performance as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Preparation of Intermediate I

[0034]

[0035] Under nitrogen protection, 0.58mol of 2-bromo-4-picoline, 0.6mol of 4-methylphenylboronic acid, 1.35mmol of Pd(dppf)Cl2 , 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, the organic phase was washed with saturated brine and water successively, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a white solid intermediate I for subsequent use. The yield of intermediate I was 92.4%.

[0036] 2) Preparation of Intermediate II

[0037]

[...

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), all the other operations are with embodiment 1, finally obtain the yield result of intermediate II 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 an iridium complex with photocatalytic performance as well as a preparation method and application thereof, the molecular formula of the iridium complex is C38H30F12IrN4P, the iridium complex photocatalyst is prepared by taking an intermediate I formed by reaction of 2-bromo-4-methylpyridine and 4-methylphenylboronic acid as a ligand, then carrying out coordination reaction with an iridium compound to form an intermediate II, and then carrying out coordination reaction with 4, 4 '-biphenylboronic acid to form the iridium complex photocatalyst. The preparation method comprises the following steps: reacting 5, 4-bis (trifluoromethyl)-2, 2-dipyridyl or 5, 5-bis (trifluoromethyl)-2, 2-dipyridyl to obtain an intermediate III, and finally replacing chlorine in the intermediate III into PF6 by using an ammonium hexafluorophosphate aqueous solution, thereby completing the preparation. The photocatalyst is applied to an alkylation reaction with tetrahydrofuran or N-Boc pyrrolidine as a substrate, a good alkylation reaction can be conducted under the heating condition under the condition that a blue light source is additionally arranged and weak organic base exists, the metal iridium complex is high in photocatalytic efficiency, the yield of an addition product can reach about 70%, 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, and in particular relates to an iridium complex with photocatalytic performance, its preparation method and application. Background technique [0002] Due to the abundant and renewable resources of visible light, mild reaction conditions, and high efficiency, visible light photoredox catalysis has great advantages over traditional synthetic 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 photocatalytic a-alkylation has aroused great interest and developed rapidly in recent years. Visible light catalysis has developed into an organic A key technology in synthesis. [0003] Photocatalysts represented by iridium complexes have attracted widespread attention due to their excellent catalytic performance. There have been photocatalysts forme...

Claims

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Application Information

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IPC IPC(8): C07F15/00B01J31/22B01J35/00C07D207/08C07D307/12
CPCC07F15/0033B01J31/1815C07D207/08C07D307/12B01J2231/46B01J2531/827B01J35/39
Inventor 马青余晓洪郝同川吴文迪潘杰峰
Owner 联碳新材料技术(杭州)有限公司
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