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Catalyst for aqueous-phase preparation of indole nitrogen arylide and preparation method of indole nitrogen arylide

A technology for the preparation of indole nitrogen aromatics and water phases, applied in the direction of physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, chemical instruments and methods, etc., can solve the problem of no catalyst, no water phase synthesis method and other problems, to achieve the effect of simple composition, easy control of reaction conditions and wide application range

Inactive Publication Date: 2015-01-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The arylation of indole nitrogen in the organic phase is well established, but the arylation of indole nitrogen in the aqueous phase has no effective catalyst
[0006] Currently, there is no well-established aqueous phase synthesis method for nitrogen arylation reaction

Method used

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  • Catalyst for aqueous-phase preparation of indole nitrogen arylide and preparation method of indole nitrogen arylide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Cuprous iodide (8 mg, 0.04 mmol), 2,2'-bipyridine (12 mg, 0.08 mmol), betaine (94 mg, 0.8 mmol), tripotassium phosphate (170 mg, 0.8 mol), indole (47 mg, 0.4 mmol), and p-methoxyiodobenzene (187 mg, 0.8 mmol) were placed in a reaction flask, 2 ml of water were added, heated to 90 degrees Celsius, and reacted for 10 hours. Chloroform was added to the reaction system, the product was extracted with chloroform, concentrated and separated by silica gel chromatography to obtain 72 mg of indole nitrogen-p-methoxybenzene with a yield of 81%.

[0033] NMR data of indole nitrogen p-methoxybenzene: 1 H NMR (500MHz, CDCl 3 )δ7.67(d, J=8.0Hz, 1H), 7.45(d, J=8.0Hz, 1H), 7.40(d, J=9.0Hz, 2H), 7.27(d, J=3.5, 1H), 7.20(t, J=8.0, 1H), 7.14(t, J=8.0, 1H), 7.02(d, J=9.0, 2H), 6.64(d, J=3.5, 1H), 3.87(s, 3H) .

Embodiment 2

[0035] Cuprous iodide (8 mg, 0.04 mmol), 2,2'-bipyridine (12 mg, 0.08 mmol), betaine (94 mg, 0.8 mmol), tripotassium phosphate (170 mg, 0.8 mol), indole (47 mg, 0.4 mmol), and p-nitroiodobenzene (199 mg, 0.8 mmol) were placed in a reaction flask, 2 ml of water were added, heated to 90 degrees Celsius, and reacted for 10 hours. Chloroform was added to the reaction system, the product was extracted with chloroform, concentrated and separated by silica gel chromatography to obtain 90 mg of indole nitrogen-p-nitrobenzene with a yield of 95%.

[0036] NMR data of indole nitrogen p-nitrobenzene: 1 H NMR (500MHz, CDCl 3 )δ8.42-8.37(m, 2H), 7.72-7.64(m, 4H), 7.37(d, J=3.5Hz, 1H), 7.32-7.21(m, 2H), 6.76(d, J=3.5Hz , 1H).

Embodiment 3

[0038] Cuprous iodide (8 mg, 0.04 mmol), 2,2'-bipyridine (12 mg, 0.08 mmol), betaine (94 mg, 0.8 mmol), tripotassium phosphate (170 mg, 0.8 mol), indole (47 mg, 0.4 mmol), and p-chloroiodobenzene (191 mg, 0.8 mmol) were placed in a reaction flask, 2 ml of water were added, heated to 90 degrees Celsius, and reacted for 10 hours. Chloroform was added to the reaction system, the product was extracted with chloroform, concentrated and separated by silica gel chromatography to obtain 74 mg of indole nitrogen p-chlorobenzene with a yield of 82%.

[0039] NMR data of indole nitrogen p-chlorobenzene: 1 H NMR (500MHz, CDCl 3 )δ7.68(d, J=8.0Hz, 1H), 7.52-7.41(m, 5H), 7.28(d, J=3.0Hz, 1H), 7.25-7.15(m, 2H), 6.68(d, J =3.0Hz, 1H).

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Abstract

The invention discloses a catalyst for aqueous-phase preparation of indole nitrogen arylide. The catalyst comprises oxides of copper salt or copper, ligands and surface active agents according to the molar ratio of 1:(0.5-50):(0.5-50). The invention further discloses a method utilizing the catalyst to realize aqueous-phase preparation of the indole nitrogen arylide. The method includes steps of adding the catalyst, indoles or indole derivatives, iodo-arylide and alkali into water to realize nitrogen arylation reaction; and treating after the nitrogen arylation reaction so as to obtain the indole nitrogen arylide. The catalyst for the aqueous-phase preparation of the indole nitrogen arylide is cheap and environment-friendly, is simple in composition, wide in application range and easy to use, and can be used for industrialization production. Reaction conditions required by the catalyst for preparing the indole nitrogen arylide are easy to control.

Description

technical field [0001] The invention relates to the technical field of organometallic catalytic synthesis, in particular to a catalyst and a method for preparing indole nitrogen aryl compounds in water phase. Background technique [0002] The world is now entering the era of green economy. In 2009, the United Nations convened a special council to advocate the development of green economy and the Green New Deal. At the same time, countries around the world are actively proposing various economic revitalization plans to promote the development of a green economy. The United States, South Korea, Japan, the European Union and other countries have proposed development plans, and the European Union has also made active deployments. South Korea even directly called the national economic revitalization plan low-carbon green growth, and other developing countries have also made corresponding plans. my country is also very active in this process. It regards the response to the global...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07D209/08
Inventor 刘松柏周佳慧
Owner ZHEJIANG UNIV
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