CN111545247B - SBA-15 supported multiphase chiral phosphine gold catalyst and preparation method and application thereof - Google Patents
SBA-15 supported multiphase chiral phosphine gold catalyst and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a SBA-15 supported chiral phosphine gold catalyst, a preparation method and application thereof, which is characterized in that chiral phosphine ligands introduced with olefin functional groups are reacted with Me2S.AuCl to obtain a homogeneous chiral phosphine gold catalyst, the homogeneous chiral phosphine gold catalyst is supported on the surface of sulfhydryl-functionalized SBA-15 to obtain a multiphase chiral phosphine gold catalyst material, and the catalyst synthesizes furan compounds in asymmetric [2+2] cyclization reaction of 3-indole olefin and 2-oxazolidone bialkene ammonia, and has better catalytic activity and selectivity. Compared with the prior art, the catalyst has the advantages of a highly ordered two-dimensional hexagonal mesoporous structure, a larger specific surface area, uniform pore size distribution and the like, has high catalytic activity in the asymmetric [2+2] cyclization reaction of 3-indole olefin and 2-oxazolidinone bialkene ammonia, is easy to separate and can be recycled, and has great development potential and application prospect in the heterogeneous catalysis field.
Description
Technical Field
The invention relates to the technical field of chiral catalysts and applications, in particular to a preparation method of a recyclable heterogeneous SBA-15 supported chiral phosphine gold catalyst and an application of the catalyst in an asymmetric [2+2] cyclization reaction of 3-indole olefin and 2-oxazolidone bialkene ammonia.
Background
In recent years, chiral phosphine ligands and gold compounds thereof have been rapidly developed, and particularly, the chiral phosphine ligands have the most widely applied in the field of asymmetric catalysis of diene, but further development and application of chiral phosphine ligand gold compounds are limited due to the fact that gold is expensive, the preparation steps of the chiral phosphine ligands are complicated, environmental pollution is easy to cause, and the chiral phosphine ligands are difficult to store. The design and synthesis of a novel chiral phosphine ligand gold catalyst which can be recycled and is easy to store is a hot spot of current research. The most effective way to solve this problem is to select an appropriate support for the support of the homogeneous catalyst, and then attach the homogeneous catalyst to the support by constructing covalent bonds between the chiral phosphine ligand and its gold compound and the support to prepare a heterogeneous chiral catalyst of the chiral phosphine ligand gold compound.
At present, most of the research on chiral phosphine ligands and gold compounds thereof is still in homogeneous catalysis, while less research is in the heterogeneous catalysis field. Zhang Junliang group (ACS catalyst.2015, 5, 7488-7492) introduces double bond on chiral imine phosphine ligand, then carries out free radical copolymerization reaction with styrene and DVB, and further prepares an organic polymer supported chiral heterogeneous catalyst, which shows excellent catalytic performance in asymmetric [2+2] cyclization reaction of alkenone and nitrone; however, the heterogeneous catalyst is difficult to separate and the addition of auxiliary silver salt in the circulation is required, which results in serious limitation of the application of the catalyst.
The heterogeneous chiral phosphine gold catalyst in the prior art is extremely easy to oxidize and difficult to separate in the preparation process, the activity cannot be maintained after recycling, and further development and application are difficult to obtain, so that the development of the heterogeneous catalyst of the chiral phosphine ligand gold compound with simple preparation process, high stability and excellent catalytic performance has important significance for the development of the heterogeneous asymmetric catalysis field.
Disclosure of Invention
The invention aims to provide an SBA-15 supported chiral phosphine gold catalyst, a preparation method and application thereof, which are designed aiming at the defects of the prior art, wherein an olefin functional group-introduced chiral phosphine ligand is adopted to react with Me2S.AuCl to obtain a homogeneous phase chiral phosphine gold catalyst, anions are exchanged and then are supported on the surface of a sulfhydryl-functionalized SBA-15 to obtain a multiphase chiral phosphine gold catalyst material, the catalyst synthesizes furan compounds in the asymmetric [2+2] cyclization reaction of 3-indole olefin and 2-oxazolidinone binaphthyl ammonia, the catalyst has better catalytic activity and selectivity, the catalyst preparation process is simple, the free radical reaction can be initiated for grafting only by using ultraviolet lamp irradiation, the prepared catalyst is easy to separate and can be recycled, the formed multiphase phosphine gold catalyst has the advantages of a highly ordered two-dimensional hexagonal mesoporous structure, larger specific surface area, uniform pore size distribution and the like, and has great development potential and application prospect in the multiphase catalysis field.
The specific technical scheme for realizing the aim of the invention is as follows: a preparation method of an SBA-15 supported multiphase chiral phosphine gold catalyst is characterized in that an alkenyl functionalized chiral imine phosphine ligand, dimethyl sulfide gold chloride and tetrahydrofuran are mixed according to the molar volume ratio of 1mmol:1.2mmol to 1.5mmol: 5-10 mL, stirring and reacting for 2-4 h at room temperature to obtain a homogeneous phase chiral phosphine gold catalyst, and then mixing the homogeneous phase chiral phosphine gold catalyst with azodiisobutyronitrile, toluene and mercapto-functionalized SBA-15 in a molar volume ratio of 1mmol:0.6 to 0.8mmol:50 mL-60 mL:1.5 to 1.8mmol of the catalyst is mixed to carry out the synthesis reaction with the following reaction structural formula:
wherein: ar is alkyl alkene;
the synthesis reaction is irradiated by an ultraviolet lamp for 2-5 hours at room temperature, the reaction liquid is alternately washed by toluene and diethyl ether after suction filtration, and then vacuum drying is carried out for 8-12 hours at the temperature of 80-110 ℃ to obtain the product which is the SBA-15 supported multiphase chiral phosphine gold catalyst with a highly ordered two-dimensional hexagonal mesoporous structure, a larger specific surface area and uniform pore size distribution.
The alkenyl is allyl, 1-butenyl.
The application of the SBA-15 supported heterogeneous chiral phosphine gold catalyst is characterized in that the SBA-15 supported heterogeneous chiral phosphine gold catalyst is dissolved in methylene dichloride, stirred for 5-10 min at the temperature of minus 78 ℃, and then 3-indolene and 2-oxazolidone biantene ammonia are added for asymmetric [2+2] cyclization reaction of the 3-indolene and 2-oxazolidone biantene ammonia with the following reaction structural formula:
wherein: r is R 1 Is alkyl or aryl; r is R 2 Is alkyl or aryl;
the cyclization reaction temperature is-65 to-80 ℃, the reaction time is 3-8 h, the catalyst is filtered after the reaction is finished, the filtrate is washed for a plurality of times by acetone and then is combined with an organic phase, then the product is a chiral indole-containing four-membered ring compound through drying, suction filtration, concentration and column chromatography, the filtered catalyst can be reused after washing and drying, and the molar volume ratio of 3-indole olefin, 2-oxazolidone biantene ammonia to the multiphase chiral phosphine gold catalyst to dichloromethane is 1mmol:1.2 to 1.3mmol:0.3 to 0.5mmol: 2-10 mL.
Compared with the prior art, the catalyst has the advantages of a highly ordered two-dimensional hexagonal mesoporous structure, a larger specific surface area, uniform pore size distribution and the like, has high catalytic activity in the asymmetric [2+2] cyclization reaction of 3-indolene and 2-oxazolidone biantene ammonia, has simple catalyst synthesis process, can initiate free radical reaction for grafting by using ultraviolet lamp irradiation, and has the advantages of easy separation and recycling, good recycling performance, environmental-friendly heterogeneous catalyst and great development potential and application prospect in the heterogeneous catalysis field.
Drawings
FIG. 1 is an X-ray diffraction pattern of the product prepared in example 1;
FIG. 2 is a product N prepared in example 1 2 Adsorption-desorption isotherm plot.
Detailed Description
The present invention will be described in further detail with reference to the following examples.
Example 1
Preparation of chiral phosphine ligand
1g (5.0 mmol) of the phosphine sulfinamide ligand and 20mL of methylene dichloride are weighed into a flask, placed into a reaction bath with a low temperature and constant temperature of 48 ℃ below zero, 10mmol of propylene is slowly dripped into a round bottom flask, the device is transferred to room temperature for reaction for 9 hours after the dripping is finished, and NH is used 4 The reaction was quenched with Cl solution, diluted with 3X 10mL ethyl acetate, and the reaction solution was extracted, dried over anhydrous sodium sulfate, spin-dried, and separated by column chromatography to give 0.9g of the product as an allylic functionalized chiral phosphine ligand.
Preparation of homogeneous chiral phosphine gold catalyst
Under argon atmosphere, 425mg of the prepared allyl functionalized chiral phosphine ligand and 52mg of dimethyl sulfide gold chloride are weighed and placed in a flask, after three times of air exchange, 50mL of anhydrous DCM solution is added, after stirring for 2 hours at room temperature, 5mol% of AgOTf is added, and then NH is used 4 Quenching the reaction with Cl solution, and addingDiluting with 3X 10mL ethyl acetate, extracting the reaction liquid, drying with anhydrous sodium sulfate, spin drying and column chromatography to obtain 0.8g of product which is the homogeneous phase chiral phosphine gold catalyst after anion exchange.
(III) immobilization of heterogeneous chiral phosphine gold catalyst
Under argon atmosphere, 515mg of the prepared homogeneous chiral phosphine gold catalyst, 1.0g of mercapto-functionalized SBA-15 and 54mg of AIBN are weighed into a flask, 100mL of toluene is added after vacuumizing, the mixture is irradiated for 5 hours at room temperature by an ultraviolet lamp, reaction liquid is alternately washed by toluene and diethyl ether after being subjected to suction filtration, and then the mixture is dried for 6 hours at 80 ℃ under vacuum, so that 0.9g of heterogeneous chiral phosphine gold catalyst with the product of SBA-15 is obtained.
Referring to figure 1, the product is characterized by X-ray diffraction, and the obtained material is proved to be of a highly ordered two-dimensional hexagonal structure, and the structure of the material is not destroyed in the material modification process.
Referring to figure 2, the specific surface areas of the above products are 471m respectively by isothermal characterization of nitrogen adsorption-desorption 2 Per gram, pore volume of 0.58cm 3 /g。
Example 2
Preparation of chiral phosphine ligand
Weighing 5.0mmol of sulfinamide phosphine ligand and 20mL of dichloromethane, placing in a flask, placing in a reaction bath with constant temperature of-48 ℃, slowly dripping 10mmol of 1-butenyl magnesium bromide into the flask, transferring the device to room temperature for reaction for 8h after dripping, and then using NH 4 The reaction was quenched with Cl solution, diluted with 3X 10mL of ethyl acetate, and the reaction solution was extracted, dried over anhydrous sodium sulfate, spin-dried, and separated by column chromatography to give 0.8g of the product as a 1-butenyl functionalized chiral phosphine ligand.
Preparation of homogeneous chiral phosphine gold catalyst
460mg of the prepared 1-butenyl propyl functionalized chiral phosphine ligand and 52mg of dimethyl sulfide gold chloride are weighed under argon atmosphere, placed in a flask, after three times of air extraction, 50mL of anhydrous DCM solution is added, 5mol% AgOTf is added after stirring for 2 hours at room temperature, then NH4Cl solution is used for quenching reaction, 3X 10mL of ethyl acetate is added for dilution, the reaction solution is extracted, dried by anhydrous sodium sulfate, spin-dried and separated by column chromatography, and 0.65g of product is obtained as a homogeneous chiral phosphine gold catalyst after anion exchange.
(III) immobilization of heterogeneous chiral phosphine gold catalyst
530mg of the prepared homogeneous chiral phosphine gold catalyst, 1.0g of mercapto-functionalized SBA-15 and 54mg of AIBN are weighed in a flask under argon atmosphere, 100mL of toluene is added after vacuumizing, the mixture is irradiated for 5 hours at room temperature by an ultraviolet lamp, reaction liquid is alternately washed by toluene and diethyl ether after being subjected to suction filtration, and then the mixture is dried for 6 hours at 80 ℃ under vacuum, so that 1.2g of heterogeneous chiral phosphine gold catalyst with the product of SBA-15 is obtained.
Example 3
Under argon atmosphere, 5.5mol% of the prepared SBA-15 supported heterogeneous chiral phosphine gold catalyst and 5mL of DCM solution are weighed and mixed to form a reaction system, the reaction system is stirred for 15min at the temperature of minus 78 ℃, then 0.4mmol of 3-indolene, 1.1 eq.2-oxazolidone bianenolamine and 3mL of DCM solution are mixed and then cooled to minus 78 ℃ to be added into the reaction system, the reaction is carried out for 4 hours at the temperature of minus 78 ℃, the catalyst is filtered after the reaction is finished, the filtrate is washed three times by acetone, the organic phases are combined, and then the mixture is dried in vacuum, filtered in suction, and concentrated and subjected to column chromatography to obtain 0.07g of product which is chiral indole-containing four-ring compound, the yield is 91%, the ee value is 90%, and the filtered catalyst can be reused after washing and drying. The recovered catalyst still maintains higher catalytic activity, and can still obtain chiral indole-containing four-membered ring compounds with a yield of 90% and an ee value of 89% when the catalyst is recycled for 6 times.
The present invention is further described in terms of the above embodiments, which should not be construed as limiting the scope of the invention, but rather should be construed according to the appended claims.
Claims (3)
1. A preparation method of an SBA-15 supported heterogeneous chiral phosphine gold catalyst is characterized in that an alkenyl functionalized chiral imine phosphine ligand, dimethyl sulfide gold chloride and tetrahydrofuran are mixed according to a molar volume ratio of 1mmol:1.2mmol to 1.5mmol: 5-10 mL, stirring at room temperature for reaction for 2-4 h to obtain a homogeneous phase chiral phosphine gold catalyst, and then mixing the homogeneous phase chiral phosphine gold catalyst with azodiisobutyronitrile, toluene and mercapto-functionalized SBA-15 to perform the synthesis reaction of the heterogeneous chiral phosphine gold catalyst according to the following reaction structural formula:
wherein: ar is alkyl alkene;
the mol volume ratio of the homogeneous chiral phosphine gold catalyst to the azodiisobutyronitrile, toluene and mercapto-functionalized SBA-15 is 1mmol:0.6 to 0.8mmol:50 mL-60 mL:1.5 to 1.8mmol; the synthesis reaction is irradiated by an ultraviolet lamp for 2-5 hours at room temperature, the reaction liquid is alternately washed by toluene and diethyl ether after suction filtration, and then vacuum drying is carried out for 8-12 hours at the temperature of 80-110 ℃ to obtain the product which is the multiphase chiral phosphine gold catalyst with a highly ordered two-dimensional hexagonal mesoporous structure.
2. The method for preparing the SBA-15 supported heterogeneous chiral phosphine gold catalyst according to claim 1, wherein the alkenyl is allyl and 1-butenyl.
3. The use of a catalyst prepared by a preparation method of a heterogeneous chiral phosphine gold catalyst supported by SBA-15, which is characterized in that the heterogeneous chiral phosphine gold catalyst supported by SBA-15 is dissolved in methylene dichloride, and 3-indolene and 2-oxazolidone biantene ammonia are added after stirring for 5-10 min at a temperature of minus 78 ℃ to carry out asymmetric [2+2] cyclization reaction of 3-indolene and 2-oxazolidone biantene ammonia with the following reaction structural formula:
wherein: r is R 1 Is alkyl or aryl; r is R 2 Is alkyl or aryl;
the cyclization reaction temperature is-65 to-80 ℃, the reaction time is 3-8 h, the catalyst is filtered after the reaction is finished, the filtrate is washed for a plurality of times by acetone and then is combined with an organic phase, then the product is a chiral indole-containing four-membered ring compound through drying, suction filtration, concentration and column chromatography, the filtered catalyst can be reused after washing and drying, and the molar volume ratio of 3-indole olefin, 2-oxazolidone biantene ammonia to the multiphase chiral phosphine gold catalyst to dichloromethane is 1mmol:1.2 to 1.3mmol:0.3 to 0.5mmol: 2-10 mL.
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