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A method based on electrochemical synthesis of tetraarylhydrazines

A compound, the technology of arylhydrazine, applied in the field of electrochemical organic synthesis, can solve the problems of unfriendly environment, small scope of application of substrates, expensive catalysts, etc., and achieve simple and easy-to-obtain raw materials, wide application scope of substrates, and simple reaction system Efficient effect

Active Publication Date: 2022-03-22
QILU UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In view of the deficiencies in the prior art, especially in the existing synthetic methods of tetraarylhydrazine compounds, there are shortcomings such as the need for additional chemical oxidants or the catalysis of transition metals, the scope of substrate application is small, the catalyst is expensive, and the environment is not friendly. The present invention provides A method for synthesizing tetraarylhydrazine compounds with simple and easy-to-obtain raw materials, simple reaction operation, wide substrate applicability, high atom utilization rate, green and efficient

Method used

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  • A method based on electrochemical synthesis of tetraarylhydrazines
  • A method based on electrochemical synthesis of tetraarylhydrazines
  • A method based on electrochemical synthesis of tetraarylhydrazines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Add 0.25mmol of N-(4-chlorophenyl)-5-fluoropyridin-2-amine, 0.5mmol of tetrabutylammonium iodide as an electrolyte, 7.0mL of acetonitrile, and 0.5mL of methanol in a three-necked flask And a magnetic stirrer, nitrogen as a protective gas, a platinum sheet (1.0cm×1.0cm) as an anode and a cathode, turn on the power, adjust the current to 5.0mA, and react at 60°C for 10 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the crude product was purified by column chromatography. The eluent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1 to obtain a tetraarylhydrazine compound with a yield of 99%. 2a.

[0061]

[0062] The product 2a that present embodiment obtains 1 H-NMR spectrum such as figure 2 as shown, 13 C-NMR spectrum such as image 3 As shown, the NMR data are as follows:

[0063] 1 H-NMR (400MHz, CDCl 3 ): δ8.11(d, J=2.6Hz, 2H), 7.39(d, J=8.7Hz, 4H), 7.30-7.24(m, 2H), 7.22(d, J=8...

Embodiment 2

[0067] Into a three-necked flask were sequentially added 0.25 mmol of 5-fluoro-N-(p-tolyl)pyridin-2-amine, 0.5 mmol of tetrabutylammonium iodide as an electrolyte, 7.0 mL of acetonitrile, 0.5 mL of methanol, and a magnetic Stirrer, nitrogen as protective gas, platinum sheet (1.0cm×1.0cm) as anode and cathode, power on, adjust current to 5.0mA, react at 60°C for 10 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the crude product was purified by column chromatography. The eluent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1 to obtain 92% tetraarylhydrazine compound 2b, structural formula as follows:

[0068]

[0069] Product 2b 1 H-NMR spectrum such as Figure 4 as shown, 13 C-NMR spectrum such as Figure 5 As shown, the NMR data are as follows:

[0070] 1 H-NMR (400MHz, CDCl 3 ):δ8.09(d,J=2.8Hz,2H),7.35(d,J=8.4Hz,4H),7.25-7.19(m,2H),7.07(d,J=8.3Hz,4H),6.95 (dd,J=9.1,3.4Hz,2H),2.27(s,6...

Embodiment 3

[0074] 0.25mmol of N-(4-(tert-butyl)phenyl)-5-fluoropyridin-2-amine, 0.5mmol of tetrabutylammonium iodide as electrolyte, 7.0mL of acetonitrile, 0.5mL of methanol and a magnetic stirrer, nitrogen as a protective gas, platinum sheets (1.0cm×1.0cm) as anode and cathode, turn on the power, adjust the current to 5.0mA, and react at 60°C for 10 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the crude product was purified by column chromatography. The eluent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1 to obtain a tetraarylhydrazine compound with a yield of 95%. 2c, the structural formula is as follows:

[0075]

[0076] Product 2c 1 H-NMR spectrum such as Figure 6 as shown, 13 C-NMR spectrum such as Figure 7 As shown, the NMR data are as follows:

[0077] 1 H-NMR (400MHz, CDCl 3 ): δ8.11(d, J=2.6Hz, 2H), 7.42(d, J=8.6Hz, 4H), 7.28(d, J=8.7Hz, 4H), 7.24-7.18(m, 2H), 6.96 (dd,J=9.1,3.3Hz...

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Abstract

The invention relates to a method for electrochemically synthesizing tetraarylhydrazine compounds, belonging to the technical field of electrochemical organic synthesis. The method comprises the following steps: sequentially adding diarylamine compound, solvent, and electrolyte into an unseparated electrolytic cell, inserting an anode and a cathode, stirring, electrifying, constant current, and reacting under nitrogen conditions, and separating and purifying after the reaction is completed to obtain The product tetraarylhydrazine compounds. The present invention uses tetrabutylammonium iodide as the electrolyte reaction without adding additional metal catalysts, oxidants or acids and bases, thereby effectively avoiding the use of toxic substances, and reacting under non-toxic and harmless conditions. The reaction system is simple and efficient, and the environment friendly.

Description

technical field [0001] The invention discloses a method for electrochemically synthesizing tetraarylhydrazine compounds, belonging to the technical field of electrochemical organic synthesis. Background technique [0002] Arylhydrazine compounds are a common organic framework: tetraarylhydrazine is a unique framework structure in natural products dixiamycin A and dixiamycin B. [0003] [0004] Besides, tetraarylhydrazines can also be used as electrocatalysts. The main methods for synthesizing tetraarylhydrazines in existing reports are: (1) In 2019, Yu Wenquan et al. used the conventional catalytic oxidative coupling of secondary amines and chemical oxidants (iodine simple substances) (Org.Biomol.Chem. , 2019, 17, 3446-3450.); (2) 2017 et al described the oxidative C-C and N-N coupling reactions of diarylamines in the presence of various iron catalysts (Angew.Chem.Int.Ed., 2017, 56, 549-553); (3) recently, Stahl and his Colleagues developed an aerobic oxidative dimer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/23C25B3/05C25B3/09
CPCC25B3/23
Inventor 陈建宾吕士德
Owner QILU UNIV OF TECH
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