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Method for synthesizing biphenyl compounds under composite catalytic actions of Pd/C and crown ether
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A composite catalyst and compound technology, which is applied in the preparation of carbon-based compounds, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problem that Pd/C catalysts cannot be recycled and the yield of biphenyl compounds cannot reach more than 95%. %, high cost of biphenyl compounds, to achieve the effect of short time, mild reaction conditions and simple operation
Inactive Publication Date: 2014-04-02
HEILONGJIANG UNIV
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[0007] The present invention will solve the problem that the Pd / C catalyst used in the Pd / C catalyzed Suzuki coupling reaction in the prior art cannot be recycled, the cost of producing biphenyl compounds is high, and the yield of biphenyl compounds cannot reach more than 95% problem, and provide a kind of method that adopts palladium / carbon and crown ether composite catalysis to synthesize biphenyl compound
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specific Embodiment approach 1
[0010] Specific embodiment 1: This embodiment provides a kind of method that adopts palladium / carbon and crown ether composite catalysis to synthesize biphenyl compound, specifically completes according to the following steps:
[0011] First, the halogenated aromatic hydrocarbon and aryl boric acid as the reaction substrate are put into the reaction kettle in a molar ratio of 1: (0.8-4), then palladium / carbon and crown ether are added as a composite catalyst, and potassium carbonate is added. Then add methanol aqueous solution, and react at room temperature for 12-36 hours under the protection of inert gas, and then extract, dry, filter, concentrate in vacuum, chromatograph, and elute to obtain biphenyl compounds.
[0012] The general formula of the halogenated aromatic hydrocarbon described in this embodiment is: R can be hydrogen, 4-nitro, 4-formyl, 4-methoxy, 3,4-dimethoxy, 2-benzyloxy-4-methyl, 2-nitro-5-methoxy group or 3,4-methylenedioxy.
[0013] The general formula ...
specific Embodiment approach 2
[0027] Embodiment 2: The difference between this embodiment and Embodiment 1 is that the amount of the added palladium / carbon substance is 1-10% of the amount of the halogenated aromatic hydrocarbon substance. Others are the same as in the first embodiment.
specific Embodiment approach 3
[0028] Embodiment 3: The difference between this embodiment and Embodiment 1 or 2 is that the amount of the added palladium / carbon substance is 2-8% of the amount of the halogenated aromatic hydrocarbon substance. Others are the same as in the first or second embodiment.
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Abstract
The invention relates to a method for synthesizing biphenyl compounds under composite catalytic actions of Pd / C and crown ether, belonging to the field of synthesis of biphenyl compounds. The invention aims to solve the problems that the Pd / C catalyst used in the Pd / C catalyzed Suzuki coupling reaction can not be used cyclically, the cost for producing the biphenyl compounds is high, and the yield of the biphenyl compounds can not be higher than 95%. The method comprises the following steps: adding aryl halide and arylboric acid as reaction substrates in a mol ratio of 1:(0.8-4) into a reaction kettle; adding Pd / C and crown ether as a composite catalyst, adding potassium carbonate and adding methanol water solution; under inert gas shielding conditions, reacting at room temperature for 12-36 hours; and extracting, drying, filtering, carrying out vacuum concentration, carrying out chromatography, and eluting to obtain the biphenyl compounds. The invention is mainly used for synthesizing biphenyl compounds.
Description
technical field [0001] The invention relates to the field of synthesis of biphenyl compounds. Background technique [0002] Biphenyl compounds widely exist in natural products, such as terpenes, lignans, flavonoids, petides and alkaloids. Many biphenyl compounds have certain biological activities, such as significantly reducing serum alanine aminotransferase, reducing liver pathological damage and enhancing liver detoxification function. At the same time, the biphenyl structure is also a common structural unit of pesticides and dyes. Among them, polyaromatic hydrocarbons have been used as organic conductors, semiconductors and liquid crystal materials due to their special physical and electronic properties. Since biphenyl compounds have these functions, more and more attention has been paid to them. Therefore, it has become a task of many scientific researchers to synthesize biphenyl compounds efficiently, quickly and at low cost using new synthetic methods. [0003] The f...
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