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Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof

A carbene complex, metal iridium technology, applied in indium organic compounds, platinum group organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of difficult industrial production, harsh reaction conditions, etc. Catalytic effect, high photocatalytic efficiency

Inactive Publication Date: 2020-08-18
CHANGZHOU INST OF TECH
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Problems solved by technology

[0004] In order to solve the technical problems of harsh reaction conditions and difficult industrial production in the traditional addition reaction of terminal alkyne compounds and isatin derivatives, a metal iridium-carbene complex with photocatalytic properties and its preparation method are provided, and The metal iridium-carbene complex is applied to the addition reaction of terminal alkyne compounds and isatin derivatives

Method used

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  • Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof
  • Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof
  • Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof

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preparation example Construction

[0039] Another aspect of the embodiments of the present invention provides a method for preparing the above metal iridium-carbene complex with photocatalytic properties, comprising the following steps:

[0040] (1) Synthesis of carbene precursor pyridine-imidazolium bromide:

[0041]

[0042] Mix N-(2,4,6-trimethylphenyl)imidazole and 2-bromopyridine as shown in the structure of formula I, seal, heat up and stir the reaction under solvent-free conditions, cool to room temperature after the reaction, and obtain The first crude product, the first crude product is taken out and washed with an ether solvent and suction filtered to obtain the carbene precursor pyridine-imidazolium bromide shown in the structure of formula II;

[0043] (2) Synthesis of metal iridium-carbene complexes:

[0044]

[0045] i) Dissolve the carbene precursor pyridine-imidazolium bromide salt prepared in step (1) in a halogenated hydrocarbon solvent, then add silver oxide solids, and react for 1 h a...

Embodiment 1

[0059] (1) Synthesis of carbene precursor pyridine-imidazolium bromide:

[0060]

[0061] In a high-temperature reaction tube equipped with a magnetic stirring bar, add 18.6 grams (100 mmol) of N-(2,4,6-trimethylphenyl) imidazole solid as shown in the structure of formula I, and then add 16.5 grams (105 mmol) of 2-bromopyridine, mix well, then seal the tube, heat up to 180°C, melt and stir for 18 hours under solvent-free conditions, cool to room temperature after the reaction, and obtain the first crude product, scrape the first crude product Take it out and put it into a centrifuge tube, add diethyl ether and shake and wash the first crude product 5 times (30mL×5 times each time), filter with suction, and obtain 30.9 grams of milky white powder after drying, which is the carbene precursor shown in the structure of formula II Pyridine-imidazolium bromide, yield 90wt%;

[0062] The reaction of step (1) is a solvent-free reaction. At high temperature, the N-(2,4,6-trimethylp...

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Abstract

The invention relates to a metal iridium-carbene complex with photocatalytic performance as well as a preparation method and application thereof, the molecular formula of the metal iridium-carbene complex is C34H36Cl2IrN6PF6, and the metal iridium-carbene complex is a mononuclear-hexadentate coordination compound of a monoclinic system and belongs to a P21 / c space group; the preparation method comprises the following steps: firstly, preparing carbene precursor pyridine-imidazole bromide from N-(2, 4, 6-trimethylphenyl) imidazole and 2-bromopyridine, then reacting with silver oxide to prepare asilver-carbene intermediate complex, and finally reacting with iridium trichloride and potassium hexafluorophosphate to prepare the metal iridium-carbene complex. The complex is applied to an addition reaction of a terminal alkyne compound and an isatin derivative, a visible light source is additionally arranged, and the addition reaction can be well carried out at room temperature by weak organic base; the metal iridium-carbene complex disclosed by the invention is relatively high in efficiency when being used as a photocatalyst for the addition reaction, and the yield of an addition productis 82 wt% or above.

Description

technical field [0001] The invention relates to the technical field of synthesis and application of transition metal complexes, in particular to a metal iridium-carbene complex with photocatalytic performance and its preparation method and application. Background technique [0002] The N-heterocyclic carbene (NHC) structure has a high activity because the oxidation state of the carbene carbon atom is +2, and there are only 6 valence electrons around the carbene carbon atom, which does not reach the stable structure of the octet law. As a special reaction intermediate, cyclocarbene has very high reactivity and can form stable complexes with almost all metals. As a very strong electron donor, the carbene ligand can increase the electron density of the central metal, and the central metal can also have a certain feedback π bond to the carbene carbon atom, so that the carbene metal complex can exist stably and has high catalytic activity. . This enables the N-heterocyclic carb...

Claims

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Application Information

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IPC IPC(8): C07F15/00B01J31/22C07D209/38
CPCC07F15/0033B01J31/1815C07D209/38B01J2231/341B01J2531/827B01J35/39
Inventor 吴泽颖孟佳瑶向梅张震威魏雪姣丁琳琳王玮
Owner CHANGZHOU INST OF TECH
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