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Alkyl/alkenyl-modified difunctional biphenyl compounds and preparation method thereof

A technology for bifunctionalization of biphenyls is applied in the field of bifunctionalized biphenyls and their preparation, which can solve the problems of poor economic benefit, low efficiency, incapability of bifunctionalization and the like, and achieves simple operation, mild reaction conditions, The effect of reducing the generation of reaction waste

Inactive Publication Date: 2016-08-10
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional synthetic method cannot use the one-pot method to difunctionalize the 2- and 2' positions of biphenyl, and the traditional method to complete the difunctionalization of biphenyl usually requires multiple steps, or the introduction of directing groups for carbon-hydrogen bonds Activation, remove the directing group after obtaining the product, these methods have low efficiency and poor economic benefit

Method used

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  • Alkyl/alkenyl-modified difunctional biphenyl compounds and preparation method thereof
  • Alkyl/alkenyl-modified difunctional biphenyl compounds and preparation method thereof
  • Alkyl/alkenyl-modified difunctional biphenyl compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Palladium-catalyzed 2-iodobiphenyl reacts with chlorinated alkanes and alkenes to synthesize butylstyryl-modified biphenyl compounds, including the following steps: add a stirring bar, 0.45mg Pd(OAc ) 2 (10mol%), corresponding 2-iodobiphenyl (0.2mmol), 105μL chlorobutane (1mmol), 23μL styrene (0.2mmol), 33μL IPA (2equiv), 78mg KOAc (4.0equiv), 138mg K 2 CO 3 (5.0 equiv) and 2.0 mL of DMF, and then use a nitrogen balloon to exchange 5 times to fill the reaction tube with nitrogen. Seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 70°C for 12 hours. At the end of the reaction, the reaction tube was cooled to room temperature, the reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth, the filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator, and the obtained crude product was purified and separated by a silica gel plate. Th...

Embodiment 2

[0111] Palladium-catalyzed reaction of 2-iodobiphenyl with chlorinated alkanes and alkenes to synthesize butylstyryl-modified biphenyls:

[0112] In a 25mL Schlenk reaction tube, add a stir bar, 4.5mg Pd(OAc) 2 (10mol%), corresponding 2-iodobiphenyl (0.2mmol), 105μL chlorobutane (1mmol), 23μL styrene (0.2mmol), 33μL IPA (2equiv), 78mg KOAc (4.0equiv), 138mg K 2 CO 3 (5.0 equiv) and 2.0 mL of DMF, and then use a nitrogen balloon to exchange 5 times to fill the reaction tube with nitrogen. Then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 70°C for 12 hours. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product Purify and iso...

Embodiment 3

[0158] Mix 2-iodobiphenyl, bromo-n-butane, styrene, isopropanol, potassium acetate, potassium carbonate, and palladium acetate in a molar ratio of 1:3:1:1:2:2:0.01, and dissolve in the solvent N-methylpyrrolidone, and then exchanged 5 times with a nitrogen balloon to fill the reaction tube with nitrogen. Then seal the reaction tube with a matching polytetrafluoroethylene stopper, and place it in a magnetic stirrer at 50°C for 24 hours. At the end of the reaction, the reaction tube was removed from the heating device and cooled to room temperature. The reaction solution was diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate obtained after washing several times with ethyl acetate was concentrated with a rotary evaporator to obtain the crude product The corresponding butylated product was purified and isolated by silica gel plate, and the yield was determined by weighing. The final product is:

[0159]

[0160] The yield was 65%.

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Abstract

The invention relates to alkyl / alkenyl-modified difunctional biphenyl compounds and a preparation method thereof. The preparation method comprises the following step: by controlling the reaction temperature at 50-110 DEG C in an organic solvent, carrying out reaction on 2-iodobiphenyl, chloralkane and olefin by using the Pd element as a catalyst for 2-24 hours in the presence of an alkali, a reducer and additives, thereby obtaining the alkyl / alkenyl-modified difunctional biphenyl compounds. Compared with the prior art, the synthesis method of the alkyl / alkenyl-modified difunctional biphenyl compounds is completed for the first time. The method has the advantages of mild conditions, high yield, wide substrate application range and the like, and is simple to operate.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an alkyl- and alkenyl-modified bifunctional biphenyl compound and a preparation method thereof. Background technique [0002] Biphenyl compounds are very important chemical intermediates and are widely used in the fields of drugs, dyes, organic semiconductors, semiconductors, and liquid crystal materials. There are many traditional synthesis methods of biphenyl compounds, such as electrochemical synthesis, organometallic coupling and intramolecular coupling. However, the traditional synthetic method cannot use the one-pot method to difunctionalize the 2- and 2' positions of biphenyl, and the traditional method to complete the difunctionalization of biphenyl usually requires multiple steps, or the introduction of directing groups for carbon-hydrogen bonds Activation, after obtaining the product and then taking off the directing group, these methods have low efficiency and poor ec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04C07C2/76C07C15/52C07C15/58C07C17/269C07C25/28C07C67/293C07C69/157C07C41/30C07C43/215C07C43/166C07C67/343C07C69/76C07C69/618C07D213/16C07D333/08C07C253/30C07C255/33C07C45/68C07C49/223C07D301/27C07D303/04C07C231/12C07C233/09
CPCC07B37/04C07C2/76C07C15/52C07C15/58C07C17/269C07C25/28C07C41/30C07C43/166C07C43/215C07C45/68C07C49/223C07C67/293C07C67/343C07C69/157C07C69/618C07C69/76C07C231/12C07C233/09C07C253/30C07C255/33C07D213/16C07D301/27C07D303/04C07D333/08
Inventor 张扬会陈度伸
Owner TONGJI UNIV
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