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Photo-catalytic preparation method of bibenzyl compounds

A technology of bibenzyl compounds and compounds, which is applied in the field of artificial synthesis of bibenzyl compounds, can solve the problems that cannot be widely used in the synthesis of bibenzyl compounds, and achieve the effect of low cost and simple synthesis

Active Publication Date: 2020-02-18
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, all the above reports on bibenzyl compounds basically only have one or two examples, which cannot be widely used in the synthesis of bibenzyl compounds

Method used

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  • Photo-catalytic preparation method of bibenzyl compounds
  • Photo-catalytic preparation method of bibenzyl compounds
  • Photo-catalytic preparation method of bibenzyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] In a 10mL 15x 25mm test tube with a stir bar, add organic tungsten photocatalyst (I) (1.0 mol%), alkali, additives, solvent, and then add benzyl bromide (0.5 mmol), stopper with rubber stopper, and argon drum The bubble removes oxygen for 15 minutes. After irradiating with 410nm LEDs for 12 hours, the color of the solution became colorless. Then add 10 mL of water, extract twice with dichloromethane (20 mL), dry with anhydrous sodium sulfate, separate by column chromatography, and rinse with ethyl acetate / petroleum ether (EA / PE=1:10) to obtain 1,2 -Diphenylethane, its nuclear magnetic analysis data is: 1 H NMR(400MHz, CDCl 3 )δ7.56–7.28(m,4H), 7.23(d,J=7.3Hz,6H), 2.97(s,4H); 13 CNMR(101MHz, CDCl 3 )δ141.82,128.48,128.37,125.95,37.99ppm.

[0040] Table 1: Conditional screening optimization

[0041]

[0042] a Use dibromomethane coordinate sample calculation 1 Product yield in H NMR

Embodiment 2

[0044] In a 10mL 15x 25mm test tube with a stir bar, add organic tungsten photocatalyst (I), TBAB (0.5mmol, 1.0eq), B 2 Pin 2 (0.55mmol), K 2 CO 3 (0.5mmol, 1eq), add 5mL acetonitrile, then add benzyl bromide (0.5mmol), put a rubber stopper, and bubbling argon to remove oxygen for 15min. Irradiated with 410nm LEDs for 12 hours, the color of the solution became colorless. Then add 10 mL of water, extract twice with dichloromethane (20 mL), dry with anhydrous sodium sulfate, separate by column chromatography, and rinse with ethyl acetate / petroleum ether (EA / PE=1:10) to obtain 1,2 -Diphenylethane.

[0045] Different equivalents of organic tungsten photosensitizers were used to catalyze benzyl bromide. The results are shown in Table 1:

[0046] Table 2: Yield under different catalyst usage

[0047] Serial number The amount of catalyst Product yield 1 0.2mol%81％ 2 0.3mol%84％ 3 0.5mol%92％ 4 0.8mol%93％ 5 1.0mol%95％ 6 1.2mol%97％ 7 1.5mol%98％ 8 1.6mol%98％ 9 1.8mol%99％

[0048] It can be...

Embodiment 3

[0050] In a 10mL 15x 25mm test tube with a stir bar, add organic tungsten photocatalyst (I) (1mol%), TBAB (0.5mmol, 1.0eq), B 2 Pin 2 (0.55mmol), K 2 CO 3 (0.5mmol, 1eq), add 5mL acetonitrile, then add the benzyl bromide compound (0.5mmol) represented by formula (A), put a rubber stopper, and bubbling argon to remove oxygen for 15min. Irradiated with 410nm LEDs for 12 hours, the color of the solution became colorless. Then add 10 mL of water, extract twice with dichloromethane (20 mL), dry with anhydrous sodium sulfate, separate by column chromatography, and rinse with ethyl acetate / petroleum ether (EA / PE=1:10) to obtain the corresponding product .

[0051] Table 3: Synthesis of (B2), (B4), (B5), (B6) and (B9) under the action of organotungsten photocatalyst (I)

[0052]

[0053] (B2): 1 H NMR(500MHz, CDCl 3 )δ7.53(d,J=8.1Hz,4H), 7.20(d,J=8.1Hz,4H), 2.97(s,4H); 13 C NMR (126MHz, CDCl3) δ 146.17, 132.27, 129.28, 118.84, 110.11, 37.16ppm.

[0054] (B4): 1 H NMR(500MHz, CDCl 3 )δ7.56(...

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Abstract

The invention relates to a preparation method of bibenzyl compounds. A compound represented by a formula (A) and a compound represented by a formula (C) carry out reactions under the action of an organic tungsten catalyst and an alkali in the presence of light to generate bibenzyl compounds represented by the formula (B). The method is simple and is easy to operate. The yield is high, and the application range is wide. Moreover, the invention also provides an application of a tungsten complex in organic chemical reactions as a photocatalyst.

Description

Technical field [0001] The invention relates to the technical field of artificial synthesis of bibenzyl compounds, in particular to a method for preparing bibenzyl compounds by photocatalysis. Background technique [0002] Bibenzyl compounds are important intermediates of fine chemicals and pharmaceutical materials. Natural bibenzyl compounds are widely found in plants and are characterized by -OH and -OCH on the benzene ring. 3 , -CH 3 Many other substituents have very good pharmacological properties, including anti-cancer, anti-bacterial, anti-fever, neuroprotection, etc. The common ones are 1,2-diphenylethane, dimeric paraxylene, Erianin, and Ami hydrochloride Tilin et al. Most of the existing artificial synthesis methods for bibenzyl compounds firstly undergo wittig reaction to generate hydrocarbon compounds, and then olefin compounds are obtained through hydrogenation reaction. This method is cumbersome, so scientists have been trying to synthesize bibenzyl compounds in one ...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C253/30C07C255/51C07C17/269C07C22/08C07C25/18C07C67/343C07C69/76C07C41/30C07C43/205C07C29/34C07C33/28
CPCC07B37/00C07C253/30C07C17/269C07C67/343C07C41/30C07C29/34C07C255/51C07C22/08C07C25/18C07C69/76C07C43/2055C07C33/28
Inventor 于道鸿刘运根支志明
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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