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Iridium complex containing carboryl benzimidazole structure and its preparation method and application

A technology containing carboryl benzimidazole and carboryl benzimidazole, which is applied in the field of semi-sandwich iridium complexes and their preparation, can solve the problems of waste of reagents, environmental damage, cumbersome steps, etc., and achieve high stability , good universality and simple synthesis process

Active Publication Date: 2021-02-26
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional preparation method of chiral alcohols is mainly obtained from racemic aromatic alcohols through multi-stage resolution, which is not only cumbersome, but also wastes reagents and causes great damage to the environment

Method used

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  • Iridium complex containing carboryl benzimidazole structure and its preparation method and application
  • Iridium complex containing carboryl benzimidazole structure and its preparation method and application
  • Iridium complex containing carboryl benzimidazole structure and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of semi-sandwich iridium complex Ir containing ortho carboryl benzimidazole structure:

[0031]

[0032] At -78°C, n-BuLi (1.6M) in n-hexane (1.00 mL, 1.6 mmol) was slowly added dropwise to the o-C 2 B 10 h 10 (92.0mg, 0.64mmol) in tetrahydrofuran solution, stirred at this temperature for 30 minutes, slowly rose to room temperature and continued to react for 1 hour, then added bromobenzimidazole (126.7mg, 0.64mmol), and continued to react at room temperature for 6 Hour. Then the binuclear iridium compound [Cp*IrCl 2 ] 2 (256.0 mg, 0.32 mmol) was added to the reaction system for an additional 3 hours. After the reaction was finished, stand and filter, and dry the solvent under reduced pressure, and the obtained crude product was separated by column chromatography (petroleum ether / tetrahydrofuran=6:1) to obtain the red target product iridium (III) complex Ir (322.4 mg, yield rate 81%).

[0033] 1 H NMR (400MHz, CDCl 3 ,25℃):δ=8.03(brs,1H),7.89(d,J=7....

Embodiment 2

[0037] Iridium(III) complexes catalyze the asymmetric reduction of aryl ketones:

[0038]

[0039] The iridium complex prepared in Example 1 was used as a catalyst to catalyze the asymmetric reduction reaction of aryl ketone: in acetophenone (10mmol, 1.20g), a trivalent iridium complex (0.01mmol, 13.0 g) containing an ortho carborane structure was added mg) in ethanol solution, hydrogen was introduced under normal pressure as a reducing agent to react, the reaction temperature was 80°C, and the reaction time was 120 minutes. chiral alcohol compound C 8 h 10 O (yield 91%), ee>99%, elemental analysis: C 78.65, H 8.25 (theoretical); C 78.59, H 8.22 (actual).

Embodiment 3

[0041] Iridium(III) complexes catalyze the asymmetric reduction of aryl ketones:

[0042]

[0043] The iridium complex prepared in Example 1 is used as a catalyst to catalyze the asymmetric reduction reaction of aryl ketone: in 4-methoxyacetophenone (10mmol, 1.50g), add a trivalent iridium complex containing an ortho carborane structure (0.01mmol, 13.0mg) in ethanol solution, and feed hydrogen as a reducing agent to react, the reaction temperature is 80°C, and the reaction time is 60 minutes. After the end, the concentrated reaction solution is directly separated by silica gel column chromatography, and dried until the quality remains unchanged. , to obtain the corresponding chiral alcohol compound C 9 h 12 o 2 (96% yield), ee>99%, elemental analysis: C 71.03, H 7.95 (theoretical); C 71.00, H 7.81 (actual).

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Abstract

The invention relates to an iridium complex containing a carboryl benzimidazole structure and a preparation method and application thereof. The preparation method of the iridium complex comprises the following steps: 1) adding the n-BuLi solution to the carborane solution, and then React at room temperature for 30-60min; 2) Add bromobenzimidazole and react at room temperature for 6-8h; 3) Add [Cp*IrCl 2 ] 2 , and react at room temperature for 3‑5h, after post-treatment to obtain the iridium complex; the iridium complex is used to catalyze the asymmetric reduction of aryl ketones to prepare chiral alcohols. Compared with prior art, the present invention uses binuclear iridium compound [Cp*IrCl 2 ] 2 As a raw material, it is reacted with n-BuLi and ortho-carboryl benzimidazole to obtain a trivalent iridium complex containing an ortho-carboryl benzimidazole structure. The iridium complex has stable physical and chemical properties and Thermal stability, and the synthesis process is simple and green. It catalyzes the asymmetric reduction reaction of aryl ketones to synthesize chiral alcohols under mild conditions. It has excellent catalytic activity, enantioselectivity and high yield.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, and relates to a semi-sandwich iridium complex containing an ortho-carboryl benzimidazole structure and a preparation method and application thereof. Background technique [0002] Chiral aromatic alcohols are a class of high-tech, high-value-added products. As a class of important organic synthesis intermediates, they have been widely used in the fields of medicine and pesticides. Therefore, how to efficiently synthesize chiral alcohols has always been one of the focuses in the field of chemistry. The traditional preparation method of chiral alcohols is mainly obtained from racemized aromatic alcohols through multi-stage resolution, which not only has cumbersome steps, but also wastes reagents and causes great damage to the environment. In recent years, in order to meet the requirements of green synthesis, researchers have developed a variety of preparation methods for chiral alcohol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/00C07B53/00B01J31/22C07C29/145C07C33/22C07C41/26C07C43/23C07C201/12C07C205/19C07C33/46
CPCB01J31/2295B01J2231/643B01J2531/827C07B53/00C07B2200/07C07C29/145C07C41/26C07C201/12C07F17/00C07C33/22C07C43/23C07C205/19C07C33/46
Inventor 姚子健樊晓楠高永红邓维
Owner SHANGHAI INST OF TECH
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