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Novel organic bismuth complex, preparation method and catalytic application thereof

A technology of complexes and organic bismuth, which is applied in the field of new organic bismuth complexes and their preparation, can solve the problems of unreported catalysts of organic bismuth complexes, and achieve the effects of wide application range of substrates, mild reaction conditions, and simple reaction operations

Active Publication Date: 2019-01-15
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There is no report on the method of directly catalyzing the synthesis of organic bismuth complex catalysts

Method used

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  • Novel organic bismuth complex, preparation method and catalytic application thereof
  • Novel organic bismuth complex, preparation method and catalytic application thereof
  • Novel organic bismuth complex, preparation method and catalytic application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In a 100mL reaction tube, add 6mmol diphenylbismuth chloride (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 The group is hydrogen), 9mmol aryl boronic acid (R 14 , R 15 , R 16 , R 17 , R 18 The group is hydrogen), 5 mol% nickel acetate, 2 equivalents of potassium carbonate, vacuum backfill nitrogen three times, add 40ml toluene under nitrogen atmosphere, and react at 120°C for 12h. After the reaction, the toluene was removed under reduced pressure, and the target product was obtained by recrystallization from ethyl acetate and n-hexane with a yield of 90%.

[0032] Catalytic activity test:

[0033] Add 0.5mmol phenylacetylene (R 1 , R 2 , R 3 , R 4 , R 5 is hydrogen), 0.5mmol aniline (R 6 , R 7 , R 8 , R 9 , R 10 hydrogen), 0.015 mmol of the novel organic bismuth complex catalyst obtained in Example 1, and then 2 ml of chloroform was added, and the reaction tube was placed in an oil bath at 100° C. for 10 h. Af...

Embodiment 2

[0035] In a 100mL reaction tube, add 6mmol diphenylbismuth chloride (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 The group is hydrogen), 9mmol aryl boronic acid (R 14 , R 15 , R 17 , R 18 The group is hydrogen, R 16 For methyl), 5 mol% nickel acetate, 2 equivalents of potassium carbonate, vacuum backfill nitrogen three times, add 40ml of toluene under nitrogen atmosphere, and react at 120°C for 10h. After the reaction, the toluene was removed under reduced pressure, and the target product was obtained by recrystallization from ethyl acetate and n-hexane with a yield of 92%.

[0036] Catalytic activity test:

[0037] Add 0.5mmol phenylacetylene (R 1 , R 2 , R 4 , R 5 for hydrogen, R 3 is methyl), 0.5mmol aniline (R 6 , R 7 , R 8 , R 9 , R 10 hydrogen), 0.015 mmol of the novel organic bismuth complex catalyst obtained in Example 2, and then 2 ml of chloroform was added, and the reaction tube was placed in a heater at...

Embodiment 3

[0039] In a 100mL reaction tube, add 6mmol diphenylbismuth chloride (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 The group is hydrogen), 9mmol aryl boronic acid (R 14 , R 15 , R 17 , R 18 The group is hydrogen, R 16 Ethyl), 5 mol% nickel acetate, 2 equivalents of potassium carbonate, evacuated and backfilled with nitrogen three times, added 40ml of toluene under nitrogen atmosphere, and reacted at 120°C for 8h. After the reaction, the toluene was removed under reduced pressure, and the target product was obtained by recrystallization from ethyl acetate and n-hexane with a yield of 93%.

[0040] Catalytic activity test:

[0041] Add 0.5mmol phenylacetylene (R 1 , R 2 , R 4 , R 5 for hydrogen, R 3 is methyl), 0.5mmol aniline (R 6 , R 7 , R 8 , R 9 , R 10 hydrogen), 0.015 mmol of the novel organic bismuth complex catalyst obtained in Example 3, and then 2 ml of chloroform was added, and the reaction tube was placed in...

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Abstract

The invention relates to a novel organic bismuth complex, a preparation method and catalytic application thereof. The method is characterized in that: a common organic solvent is adopted as the reaction solvent, diphenylbismuth chloride containing a bridge type nitrogen atom ligand and cheap and easily available arylboronic acid are adopted as the raw materials, nickel acetate is employed to catalyze reaction, and the novel organic bismuth (III) complex catalyst (I) with high yield and high selectivity can be obtained. The catalyst has good stability, is recoverable, and shows excellent catalytic activity in catalyzing the hydroamination reaction of aryl alkyne and an aniline derivative. The method has the advantages of low cost, high yield, simple operation, no pollution, etc., and has feasibility in realization of industrial production.

Description

【Technical field】 [0001] The invention belongs to the field of organic synthesis and catalysis, and in particular relates to a novel organic bismuth complex and its preparation method and catalytic application. 【Background technique】 [0002] Metal organic compounds refer to compounds that contain one or more metal-carbon (M-C) bonds. Because of its wide application in synthesis, catalysis, anti-fouling, medicine, stabilizer, etc., it has attracted widespread attention. Organic bismuth compounds refer to metal organic compounds containing bismuth-carbon (Bi-C) covalent bonds. As a main group metal element, bismuth belongs to group 15 in the periodic table of elements, and its compounds usually use three 6p electrons as a bond and two 6s electrons as an inert electron pair, so trivalent bismuth compounds are relatively common. However, so far, organobismuth compounds have been rarely used as catalysts in organic synthesis. The reason may be that the stability of organic bi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/94B01J31/12C07C249/02C07C251/16
CPCB01J31/122B01J2231/32C07C249/02C07F9/94C07C251/16
Inventor 邱仁华张德奖
Owner HUNAN UNIV