CN107827693B - Method for synthesizing 1, 2-diphenylethane derivative by coupling graphene-supported palladium/platinum-catalyzed sp3C-H bond - Google Patents

Method for synthesizing 1, 2-diphenylethane derivative by coupling graphene-supported palladium/platinum-catalyzed sp3C-H bond Download PDF

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CN107827693B
CN107827693B CN201711095556.3A CN201711095556A CN107827693B CN 107827693 B CN107827693 B CN 107827693B CN 201711095556 A CN201711095556 A CN 201711095556A CN 107827693 B CN107827693 B CN 107827693B
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梁志武
王正军
许新华
肖珉
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    • C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
    • C07C2/82—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling
    • C07C2/84—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling catalytic
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    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
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    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
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    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
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Abstract

The invention discloses a novel method for constructing 1, 2-diphenylethane compounds by developing a novel graphene-loaded bimetallic palladium-platinum catalyst which is simple, convenient, efficient, free of guide groups, free of solvent participation and capable of being repeatedly used and catalyzing sp3C-H bond activation, so that the yield of target products is improved, the operation steps are simplified, and the atom utilization rate and the recycling of the catalyst are increased. Provides an economic, efficient and green way for preparing the compound. The method has the main advantages that: the experimental operation is simple, no guide group is needed, no other solvent is needed, and the catalyst can be recycled for a plurality of times.

Description

Method for synthesizing 1, 2-diphenylethane derivative by coupling graphene-supported palladium/platinum-catalyzed sp3C-H bond
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of heterogeneous catalysis organic synthesis, and particularly relates to a synthesis method for catalyzing 1, 2-diphenylethane compounds by a novel graphene-supported palladium-platinum catalytic bimetallic nano material.
[ background of the invention ]
Biaryl compounds are present in large amounts in nature, have excellent biological activity, and are widely present in drugs, dyes, organic materials, and the like. Due to the importance of biaryls, many synthetic methods have been developed over decades, such as Suzuki, Negishi, Stille, Hiyama, and Kumada coupling reactions. However, by direct activation of sp3The construction of complex biaryls by C-H bonds has been rarely studied, probably due to sp3The dissociation energy of the C-H bond is much higher than that of other pre-activated C-X bonds, making the reaction difficult to carry out. In addition, most of the reaction is homogeneous catalysis, and the catalyst is difficult to recover, so that the separation of the product is complicated, and the reaction cost is greatly increased.
In recent decades, palladium-based nanomaterials have received increasing attention. Because they have the advantages of higher catalytic activity, recyclability, high atom utilization, and no ligand assistance, as compared to commercial bulk metal catalysts. At present, it is becoming one of effective means for catalyzing C-C and C-X (X ═ N, O, S, etc.). Especially bimetallic palladium-based catalysts, have improved stability in structure and chemical composition. Therefore, the development of a novel palladium-based bimetallic nano material for catalytically activating sp3C-H without a guiding group to construct a C-C bond has profound theoretical and practical significance.
[ summary of the invention ]
The invention aims to develop a novel method for constructing 1, 2-diphenylethane compounds by catalyzing activation of sp3C-H bonds through developing a novel graphene-loaded bimetallic palladium-platinum catalyst which is simple, convenient, efficient, free of guide groups, free of participation of solvents and reusable, so that the yield of target products is improved, the operation steps are simplified, the atom utilization rate is increased, and the catalyst is recycled.
In order to achieve the above purpose, the invention provides the following technical scheme:
a method for synthesizing 1, 2-diphenylethane compounds uses phenethylene compounds as raw materials, uses prepared novel graphene loaded bimetallic palladium-platinum alloy nano materials as catalysts, and obtains target compounds through column chromatography separation after reaction under the conditions of no guide group, no ligand and no solvent.
In the synthesis method, the catalyst is synthesized by taking chloropalladate and chloroplatinic acid as precursors and formic acid as a reducing agent under the condition of no other additives (including a surfactant, a polymer, a template and the like). The prepared catalyst is characterized by test means such as SEM, TEM, Raman, TGA and the like.
In the above synthesis method, the addition amount of the catalyst is 1-4mg, and the amount of the oxidant DTBP is 146-438 mg.
In the above synthesis method, the raw material phenethyl compound is preferably selected from phenethyl, toluene, propylbenzene, butylbenzene, isopropylbenzene, sec-butylbenzene, p-xylene, o-xylene, m-xylene, mesitylene, p-chlorotoluene, o-methoxytoluene, 2-methylnaphthalene, 2- (4-tolyl) pyridine, and the like.
In the above synthesis method, the catalytic reaction conditions are as follows: reacting for 10-24 hours at 25-120 ℃.
The synthesis method provided by the invention opens up a new way with economic steps, simple path, high efficiency and greenness for the preparation of the 1, 2-diphenylethane compounds, and has the advantages that: wide raw material sources, high selectivity and yield of target products, mild reaction conditions, simple and convenient reaction operation, repeatedly recyclable catalyst, wide substrate application range and the like.
[ description of the drawings ]
FIG. 1 shows a synthetic scheme of 1, 2-diphenylethane compounds provided by the present invention.
[ detailed description ] embodiments
The synthesis route of the method for catalytically synthesizing 1, 2-diphenylethane compounds provided by the invention is shown in the attached figure 1: placing raw materials of phenethyl compounds, catalysts and the like into a reaction vessel, adding an oxidant, reacting for 10-24 hours at the temperature of 25-120 ℃, and separating by column chromatography after the reaction is finished to obtain a target product.
The invention is further illustrated below with reference to specific preparation examples:
preparation example 1
A10 mL reaction tube was charged with phenylethane (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) and reacted at 120 ℃ for 10 h. After the reaction is finished, filtering, concentrating and separating by column chromatography to obtain the 2, 3-diphenyl butane with the yield of 96 percent.
Preparation example 2
Toluene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged into a 10mL reaction tube and reacted at 120 ℃ for 10 hours. After the reaction is finished, filtering, concentrating and separating by column chromatography to obtain the 1, 2-diphenylethane with the yield of 94 percent.
Preparation example 3
To a 10mL reaction tube were added propylbenzene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) and reacted at 120 ℃ for 10 h. After the reaction is finished, filtering, concentrating and separating by column chromatography to obtain the 3, 4-diphenylpentane with the yield of 91%.
Preparation example 4
Butylbenzene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged into a 10mL reaction tube and reacted at 120 ℃ for 24 h. After the reaction is finished, filtering, concentrating and separating by column chromatography to obtain the 4, 5-diphenyl octane with the yield of 89%.
Preparation example 5
Cumene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were added to a 10mL reaction tube and reacted at 120 ℃ for 10 h. After the reaction is finished, filtering, concentrating and separating by column chromatography to obtain the 2, 3-dimethyl-2, 3-diphenylbutane with the yield of 85 percent.
Preparation example 6
Sec-butylbenzene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged into a 10mL reaction tube and reacted at 120 ℃ for 10 h. After the reaction, the mixture was filtered, concentrated, and subjected to column chromatography to obtain 3, 4-dimethyl-3, 4-diphenylhexane with a yield of 82%.
Preparation example 7
A10 mL reaction tube was charged with p-xylene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) and reacted at 120 ℃ for 10 h. After the reaction is finished, filtering, concentrating and separating by column chromatography to obtain the 4,4' -dimethyl bibenzyl with the yield of 90 percent.
Preparation example 8
To a 10mL reaction tube were added o-xylene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) and reacted at 120 ℃ for 10 h. After the reaction, the reaction mixture was filtered, concentrated, and separated by column chromatography to obtain 2-bis (2-methylphenyl) ethane with a yield of 88%.
Preparation example 9
A10 mL reaction tube was charged with m-xylene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) and reacted at 120 ℃ for 10 h. After the reaction, the mixture was filtered, concentrated, and subjected to column chromatography to obtain 1, 2-bis (3-methylphenyl) ethane with a yield of 91%.
Preparation example 10
Into a 10mL reaction tube were added mesitylene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) and reacted at 120 ℃ for 10 h. After the reaction, the mixture was filtered, concentrated, and subjected to column chromatography to obtain 1, 2-bis (3, 5-dimethylphenyl) ethane with a yield of 90%.
Preparation example 11
P-chlorotoluene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged into a 10mL reaction tube and reacted at 120 ℃ for 10 hours. After the reaction, the reaction mixture was filtered, concentrated, and subjected to column chromatography to obtain 1, 2-bis (4-chlorophenyl) ethane in a yield of 87%.
Preparation example 12
To a 10mL reaction tube were added o-methoxytoluene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) and reacted at 120 ℃ for 10 h. After the reaction, the mixture was filtered, concentrated, and subjected to column chromatography to obtain 1, 2-bis (2-methoxyphenyl) ethane with a yield of 84%.
Preparation example 13
2-methylnaphthalene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged into a 10mL reaction tube and reacted at 120 ℃ for 24 hours. After the reaction, the mixture was filtered, concentrated, and subjected to column chromatography to obtain 1, 2-bis (2-naphthyl) ethane with a yield of 82%.
Preparation example 14
2- (4-tolyl) pyridine (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged in a 10mL reaction tube and reacted at 120 ℃ for 10 hours. After the reaction, the reaction mixture was filtered, concentrated, and subjected to column chromatography to obtain 1, 2-bis (4- (2-pyridylphenyl) ethane in a yield of 77%.
Preparation example 15
2-isopropylnaphthalene (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged into a 10mL reaction tube and reacted at 120 ℃ for 24 hours. After the reaction is finished, the reaction product is filtered, concentrated and separated by column chromatography to obtain the 2, 3-dimethyl dinaphthyl butane with the yield of 73 percent.
Preparation example 16
4-isopropylbiphenyl (10mmol, excess), catalyst (Pd @ Pt PNSs/RGO, 4mg), DTBP (5mmol, 5equiv) and NaOAC (1mmol, 1equiv) were charged in a 10mL reaction tube and reacted at 120 ℃ for 24 hours. After the reaction, the reaction mixture was filtered, concentrated, and subjected to column chromatography to obtain 2, 3-dimethylbis (1, 1' -biphenylyl) butane with a yield of 75%.
The above examples are merely illustrative of specific embodiments of the present invention, and are not to be construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (6)

1. A novel method for constructing 1, 2-diphenylethane compounds I by catalyzing sp3C-H bond activation with graphene supported bimetallic palladium-platinum catalyst is characterized in that target compounds are obtained by taking graphene supported bimetallic palladium-platinum nano-materials as catalyst and taking compounds II as raw materials, and a reaction catalysis system can be repeatedly used for many times,
Figure DEST_PATH_IMAGE001
r is selected from alkyl, phenyl, Cl, methoxy and H;
R1selected from H and alkyl;
R2selected from H and alkyl;
the reaction is carried out in the absence of a solvent.
2. The method of claim 1, wherein the reaction does not require the participation of a directing group.
3. The method according to claim 1, wherein the graphene supported bimetallic palladium-platinum catalyst is synthesized by taking chloropalladic acid and chloroplatinic acid as precursors and formic acid as a reducing agent under the condition of no other additive.
4. The method of claim 1, wherein the amount of the graphene supported bimetallic palladium-platinum catalyst ranges from 1 to 10 mg.
5. The process according to claim 1, wherein the compound II is selected from the group consisting of phenylethane, toluene, propylbenzene, butylbenzene, isopropylbenzene, sec-butylbenzene, p-xylene, o-xylene, m-xylene, p-chlorotoluene, o-methoxytoluene, 4-isopropylbiphenyl.
6. The method of claim 1, wherein the reaction conditions are: reacting for 10-24h at 50-140 ℃.
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An unprecedented oxidative intermolecular homo coupling reaction between two sp3C–sp3C centers under metal-free condition;Santosh K. Sahoo;《Tetrahedron Letters》;20160627;第57卷(第31期);表2，图3 *
Hydrogen Abstraction from the isomeric cymenes;A. Sulpizio et al.;《Tetrahedron》;19891231;第45卷(第23期);第7545-7552页 *
石墨烯上氧化镍隔离的高分散钯催化剂的制备及其在suzuki偶联反应中的应用;聂仁峰等;《第十四届全国青年催化学术会议会议论文集》;20130728;第517-518页 *

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