CN103881097A - Imidazolium salt carbene palladium catalyst with phase-transfer catalysis performance and preparation method of catalyst - Google Patents
Imidazolium salt carbene palladium catalyst with phase-transfer catalysis performance and preparation method of catalyst Download PDFInfo
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Abstract
The invention discloses an imidazolium salt carbene palladium catalyst with a phase-transfer catalysis performance and a preparation method of the catalyst. The catalyst has the following advantages: (1) the catalyst is relatively simple to prepare, and is easily further modified as almost hydroxyls are distributed on the surface; the catalyst has high thermodynamic stability, representing that the catalyst has abundant hydroxyls for the convenience of re-immobilizing the homogeneous catalyst to be recycled, so that the catalyst is further applied to the fields of catalysis, sewage treatment and the like; (2) the catalyst can be better dispersed in a reaction system to promote reaction, so that the reaction rate is further increased; (3) the catalyst disclosed by the invention is designed and prepared based on the imidazolium salt carbene palladium catalyst, compared with conventional imidazolium salt materials or catalysts, the catalyst further has the phase-transfer catalysis function and strong match compatibility.
Description
Technical field
The present invention relates to a kind of imidazole salts type Cabbeen palladium catalyst with phase-transfer catalysis performance and preparation method thereof.
Background technology
The silicon materials preparation of imidazole salts type organic inorganic hybridization is simple, is easy to modification.As a kind of carrier of functionalization, itself there is the effect of phase-transfer catalyst, be applied to heterogeneous catalytic reaction, respond well.Have higher thermodynamic stability, showing has abundant hydroxyl, is convenient to the immobilized of homogeneous catalyst.Hydroxyl is distributed in surface more, the avtive spot of the heterogeneous catalyst of preparing distribute more extensively evenly, and material has open microtexture, is convenient to substrate and is also conducive to stereoselective raising approaching time.As a kind of carrier of functionalization, this material has had certain application in asymmetric catalysis field.Ionic liquid is widely studied as the eco-friendly reaction medium of one.Babak Karimi seminar uses 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion under acidic conditions, after self-service dress, to obtain imidazole salts type organic inorganic hybridization silicon materials first, by the immobilized metal Yb of physisorphtion (OTf)
3afterwards for asymmetric Strecker reaction, show good catalytic performance and realized recycle (Chem.Commun., 2010,46,6947 – 6949) of catalyzer.Recently, Andrew J.Hunt seminar utilizes the two silicon of imidazoles sources to synthesize load the PMO type mesoporous silicon material of Pd and Ru metal, be applied to respectively Suzuki-Miyaura reaction (Chem.Eur.J., 2010,16,8047 – 8053) and the oxidation (Org.Biomol.Chem. of alcohol, 2011,9,7420 – 7426), all show good catalytic performance.Research from these to imidazole salts type hybrid silicon material can know that this material has higher thermostability, itself has the function of phase-transfer catalyst, is easy to realize by the method for grafting or copolymerization with other silicon sources the functional modification of material.But the method for physical adsorption not as chemical covalent linkage immobilized firmly, catalyzer easily runs off in the time recycling.
Self can be used as carbenes imidazole salts, with Pd (OAc)
2mol ratio coordination in 1: 2, forms N-heterocyclic carbine palladium catalyst (Tetrahedron., 2008,64,4637-4643), is applied to Suzuki reaction and Heck reaction.But the phase-transfer catalysis function of imidazole salts type silicon materials does not well embody, rate of catalysis reaction is not high yet.Prior, the effect of the phase-transfer catalyst of imidazole salts type hybrid silicon material improves catalytic efficiency and is arranged in two-phase with chiral centre mates compatibility and also can not well embody.
Given this catalyzer that, design and preparation have more phase-transfer catalysis function and mate more by force compatible imidazole salts type hybrid silicon material becomes the patent technical issues that need to address of the present invention.
Summary of the invention
The present invention seeks to design and preparation and have more phase-transfer catalysis function and the strong catalyzer (NHC-Pd-IFOIHS) that mates compatible imidazole salts type hybrid silicon material.
Technical scheme of the present invention is:
A preparation method with the imidazole salts type Cabbeen palladium catalyst (NHC-Pd-IFOIHS) of phase-transfer catalysis performance, comprises the following steps:
(1) by Pd (OAc)
2be dissolved in anhydrous THF, add 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion, stir 1.5-2h at 20-25 ℃;
(2) then at 65-70 ℃ of backflow 4-6h, removal of solvent under reduced pressure, obtain N-heterocyclic carbine palladium compound (Pd-NHC), then under argon shield, by the N-heterocyclic carbine palladium compound (Pd-NHC) and 1 obtaining, 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion joins in deionized water and dilute hydrochloric acid and dissolves, and stirs 12-24h at 40-45 ℃;
(3) reaction mixture is proceeded in tetrafluoroethylene high pressure water heating kettle, static reaction 48-72h in the baking oven of 100-110 ℃, from water heating kettle takes out, use again deionized water and washing with alcohol, finally be placed in 50-55 ℃ of vacuum drying oven dry, obtaining khaki color powder is NHC-Pd-IFOIHS target catalyzer.
In step (1), Pd (OAc)
2with the mol ratio in 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion silicon source be 1: 2-4.
In step (2), the mol ratio of N-heterocyclic carbine palladium compound (Pd-NHC) and 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion is 1: 1-8.
In step (1), the preparation method of 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion is:
Imidazole natrium is dissolved in anhydrous THF, adds 3-iodine propyl trimethoxy silicane, under argon shield, 65-70 ℃ is stirred 12-14h; After cool to room temperature, decompression is spin-dried for solvent, adds dry toluene and 3-iodine propyl trimethoxy silicane lucifuge backflow 36-48h; After reaction finishes, with dry toluene washing gained mixture, then with anhydrous methylene chloride extraction, upper solution vacuum is spin-dried for, obtains 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion.
The present invention is first by Pd (OAc)
2with 1,3-bis-(3-trimethoxy silicon propyl group) carries out coordination in imidazole salts iodide ion silicon source and obtains the compound (Pd-NHC) of N-heterocyclic carbine palladium, then respectively again with 1,3-bis-(3-trimethoxy silicon propyl group) carries out copolymerization in imidazole salts iodide ion silicon source, select containing with the part silicon source and 1 of palladium metal coordination, 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion silicon source, as silicon source reagent, finally synthesizes based on imidazole salts type Cabbeen palladium catalyst (NHC-Pd-IFOIHS).
Gained catalyzer of the present invention has the following advantages: (1) this catalyzer preparation is relatively simple, is easy to further modification because hydroxyl is distributed in surface more.Have higher thermodynamic stability, showing has abundant hydroxyl, is convenient to the again immobilized of homogeneous catalyst, facilitates recycling, and then can be widely used in the every field such as catalysis, sewage disposal.(2) this catalyzer can be scattered in reaction system preferably, promotes the carrying out of reaction, and speed of reaction is further increased.(3) the present invention design and preparation have more phase-transfer catalysis function and coupling compatibility more by force based on imidazole salts type Cabbeen palladium catalyst with respect to traditional imidazole salts shaped material or catalyzer.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart based on imidazole salts type Cabbeen palladium catalyst prepared by the present invention.
Fig. 2 is catalyzer scanning electron microscope (SEM) photograph (SEM) and the chemical mapping graph (Mapping) of embodiment 3.
Fig. 3 is characterizing based on imidazole salts type Cabbeen palladium catalyst (NHC-Pd-IFOIHS) is final of embodiment 3
13c CP MAS NMR spectrogram.
Embodiment
Below in conjunction with embodiment, the present invention is specifically described, is necessary to be pointed out that at this present invention is only used to further illustrate the present invention, can not be interpreted as limiting the scope of the invention.
Embodiment 1
(1) in dry Schlenk bottle; after adding 1.8g (20mmol) imidazole natrium, add the anhydrous THF of 120mL to dissolve; add again after 5.8g (20mmol) 3-iodine propyl trimethoxy silicane under argon shield; 65-70 ℃ is stirred 12-14h, and rotating speed is 1000-1200r/min.After reaction finishes, cool to room temperature final vacuum is spin-dried for solvent, adds 100mL dry toluene and 5.8g (20mmol) 3-iodine propyl trimethoxy silicane lucifuge backflow 36-48h.After reaction finishes, mixture is transferred in separating funnel, with 50mL dry toluene purging compound, again with 30mL anhydrous methylene chloride extraction three times, salt is in lower floor, upper solution is transferred in dry round-bottomed flask, after vacuum is spin-dried for, can obtains i.e. 1,3-bis-(3-trimethoxy silicon propyl group) the imidazole salts iodide ion of yellow viscose ionic liquid.
(2) by the 5.4g (9mmol) 1 obtaining in step (1), 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion and 1g (4.5mmol) Pd (OAc)
2be dissolved in anhydrous THF and join together in dry Schlenk bottle, stir 1.5-2h at 20-25 ℃, rotating speed is 800-1000r/min.
(3) Schlenk bottle in step (2) is moved to 65-70 ℃ of oil bath pan, vigorous stirring 4-6h, rotating speed is 1300-1500r/min.After reaction finishes, removal of solvent under reduced pressure can obtain N-heterocyclic carbine palladium compound (Pd-NHC).
(4) then under argon shield; by 5.2g (4.5mmol) the N-heterocyclic carbine palladium compound (Pd-NHC) obtaining in step (3) and 2.7g (4.5mmol) 1; 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion joins in 20mL deionized water and 100mL1-2M dilute hydrochloric acid and dissolves; in 40-45 ℃ of oil bath pan, stir 12-24h, rotating speed is 1000-1200r/min.
(5) finally proceed in tetrafluoroethylene high pressure water heating kettle static reaction 48-72h in the baking oven of 100-110 ℃ by obtaining reactant in step (4).
(6) product step (5) being obtained is poured in Büchner funnel, use successively 100mL deionized water and 100mL washing with alcohol, repeat this operation 3-5 time, after being finally dried in 50-55 ℃ of vacuum drying oven, obtaining khaki color powder is NHC-Pd-IFOIHS target catalyzer.
Fig. 1 is the synthetic schematic diagram of preparation based on imidazole salts type Cabbeen palladium catalyst (NHC-Pd-IFOIHS).
Embodiment 2
(1) in dry Schlenk bottle; after adding 1.8g (20mmol) imidazole natrium, add the anhydrous THF of 120mL to dissolve; add again after 5.8g (20mmol) 3-iodine propyl trimethoxy silicane under argon shield; 65-70 ℃ is stirred 12-14h, and rotating speed is 1000-1200r/min.After reaction finishes, cool to room temperature final vacuum is spin-dried for solvent, adds 100mL dry toluene and 5.8g (20mmol) 3-iodine propyl trimethoxy silicane lucifuge backflow 36-48h.After reaction finishes, mixture is transferred in separating funnel, with 50mL dry toluene purging compound, again with 30mL anhydrous methylene chloride extraction three times, salt is in lower floor, upper solution is transferred in dry round-bottomed flask, after vacuum is spin-dried for, can obtains i.e. 1,3-bis-(3-trimethoxy silicon propyl group) the imidazole salts iodide ion of yellow viscose ionic liquid.
(2) by the 5.4g (9mmol) 1 obtaining in step (1), 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion and 1g (4.5mmol) Pd (OAc)
2be dissolved in anhydrous THF and join together in dry Schlenk bottle, stir 1.5-2h at 20-25 ℃, rotating speed is 800-1000r/min.
(3) Schlenk bottle in step (2) is moved to 65-70 ℃ of oil bath pan, vigorous stirring 4-6h, rotating speed is 1300-1500r/min.After reaction finishes, removal of solvent under reduced pressure can obtain N-heterocyclic carbine palladium compound (Pd-NHC).
(4) then under argon shield; by 5.2g (4.5mmol) the N-heterocyclic carbine palladium compound (Pd-NHC) obtaining in step (3) and 5.4g (9mmol) 1; 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion joins in 20mL deionized water and 100mL1-2M dilute hydrochloric acid and dissolves; in 40-45 ℃ of oil bath pan, stir 12-24h, rotating speed is 1000-1200r/min.
(5) finally proceed in tetrafluoroethylene high pressure water heating kettle static reaction 48-72h in the baking oven of 100-110 ℃ by obtaining reactant in step (4).
(6) product step (5) being obtained is poured in Büchner funnel, use successively 100mL deionized water and 100mL washing with alcohol, repeat this operation 3-5 time, after being finally dried in 50-55 ℃ of vacuum drying oven, obtaining khaki color powder is NHC-Pd-IFOIHS target catalyzer.
Embodiment 3
(1) in dry Schlenk bottle; after adding 1.8g (20mmol) imidazole natrium, add the anhydrous THF of 120mL to dissolve; add again after 5.8g (20mmol) 3-iodine propyl trimethoxy silicane under argon shield; 65-70 ℃ is stirred 12-14h, and rotating speed is 1000-1200r/min.After reaction finishes, cool to room temperature final vacuum is spin-dried for solvent, adds 100mL dry toluene and 5.8g (20mmol) 3-iodine propyl trimethoxy silicane lucifuge backflow 36-48h.After reaction finishes, mixture is transferred in separating funnel, with 50mL dry toluene purging compound, again with 30mL anhydrous methylene chloride extraction three times, salt is in lower floor, upper solution is transferred in dry round-bottomed flask, after vacuum is spin-dried for, can obtains i.e. 1,3-bis-(3-trimethoxy silicon propyl group) the imidazole salts iodide ion of yellow viscose ionic liquid.
(2) by the 5.4g (9mmol) 1 obtaining in step (1), 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion and 1g (4.5mmol) Pd (OAc)
2be dissolved in anhydrous THF and join together in dry Schlenk bottle, stir 1.5-2h at 20-25 ℃, rotating speed is 800-1000r/min.
(3) Schlenk bottle in step (2) is moved to 65-70 ℃ of oil bath pan, vigorous stirring 4-6h, rotating speed is 1300-1500r/min.After reaction finishes, removal of solvent under reduced pressure can obtain N-heterocyclic carbine palladium compound (Pd-NHC).
(4) then under argon shield; by 5.2g (4.5mmol) the N-heterocyclic carbine palladium compound (Pd-NHC) obtaining in step (3) and 10.8g (18mmol) 1; 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion joins in 20mL deionized water and 100mL1-2M dilute hydrochloric acid and dissolves; in 40-45 ℃ of oil bath pan, stir 12-24h, rotating speed is 1000-1200r/min.
(5) finally proceed in tetrafluoroethylene high pressure water heating kettle static reaction 48-72h in the baking oven of 100-110 ℃ by obtaining reactant in step (4).
(6) product step (5) being obtained is poured in Büchner funnel, use successively 100mL deionized water and 100mL washing with alcohol, repeat this operation 3-5 time, after being finally dried in 50-55 ℃ of vacuum drying oven, obtaining khaki color powder is NHC-Pd-IFOIHS target catalyzer.
Fig. 2 is catalyzer scanning electron microscope (SEM) photograph (SEM) and the chemical mapping graph (Mapping) of the present embodiment, from Electronic Speculum figure, can obviously find out and synthesize a kind of size at 600nm left and right nano particle balls, can find that from chemical mapping graph the active centre of palladium is evenly distributed in this nano particle spherical structure.
Fig. 3 is characterizing based on imidazole salts type Cabbeen palladium catalyst is final of the present embodiment
13c CPMAS NMR spectrogram, as seen from the figure, obvious characteristic peaking displacement study 172.5ppm place occurs, this phenomenon can illustrate stable bond of palladium metal and N-heterocyclic carbine qualitatively, thereby shows successfully to prepare based on imidazole salts type Cabbeen palladium catalyst (NHC-Pd-IFOIHS).And this catalyzer has all shown good activity in catalysis Suzuki reaction and Heck reaction, has the fastest speed of reaction simultaneously, and therefore the present embodiment is considered to optimal catalyst.
Embodiment 4
(1) in dry Schlenk bottle, after adding 1.8g (20mmol) imidazole natrium, add the anhydrous THF of 120mL to dissolve, add again after 5.8g (20mmol) 3-iodine propyl trimethoxy silicane under argon shield, 65-70 ℃ is stirred 12-14h, and rotating speed is 1000-1200r/min.After reaction finishes, cool to room temperature final vacuum is spin-dried for solvent, adds 100mL dry toluene and 5.8g (20mmol) 3-iodine propyl trimethoxy silicane lucifuge backflow 36-48h.After reaction finishes, mixture is transferred in separating funnel, with 50mL dry toluene purging compound, again with 30mL anhydrous methylene chloride extraction three times, salt is in lower floor, upper solution is transferred in dry round-bottomed flask, after vacuum is spin-dried for, can obtains i.e. 1,3-bis-(3-trimethoxy silicon propyl group) the imidazole salts iodide ion of yellow viscose ionic liquid.
(2) by the 5.4g (9mmol) 1 obtaining in step (1), 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion and 1g (4.5mmol) Pd (OAc)
2be dissolved in anhydrous THF and join together in dry Schlenk bottle, stir 1.5-2h at 20-25 ℃, rotating speed is 800-1000r/min.
(3) Schlenk bottle in step (2) is moved to 65-70 ℃ of oil bath pan, vigorous stirring 4-6h, rotating speed is 1300-1500r/min.After reaction finishes, removal of solvent under reduced pressure can obtain N-heterocyclic carbine palladium compound (Pd-NHC).
(4) then under argon shield; by 5.2g (4.5mmol) the N-heterocyclic carbine palladium compound (Pd-NHC) obtaining in step (3) and 21.8g (36mmol) 1; 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion joins in 20mL deionized water and 100mL1-2M dilute hydrochloric acid and dissolves; in 40-45 ℃ of oil bath pan, stir 12-24h, rotating speed is 1000-1200r/min.
(5) finally proceed in tetrafluoroethylene high pressure water heating kettle static reaction 48-72h in the baking oven of 100-110 ℃ by obtaining reactant in step (4).
(6) product step (5) being obtained is poured in Büchner funnel, use successively 100mL deionized water and 100mL washing with alcohol, repeat this operation 3-5 time, after being finally dried in 50-55 ℃ of vacuum drying oven, obtaining khaki color powder is NHC-Pd-IFOIHS target catalyzer.
The above is preferred embodiment of the present invention, but the present invention should not be confined to the disclosed content of this embodiment.Do not depart from the equivalence completing under principles of this disclosure so every or revise, all falling into the scope of protection of the invention.
Claims (5)
1. a preparation method with the imidazole salts type Cabbeen palladium catalyst of phase-transfer catalysis performance, is characterized in that, comprises the following steps:
(1) by Pd (OAc)
2be dissolved in anhydrous THF, add 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion, stir 1.5-2h at 20-25 ℃;
(2) then at 65-70 ℃ of backflow 4-6h, removal of solvent under reduced pressure, obtain N-heterocyclic carbine palladium compound (Pd-NHC), then under argon shield, by the N-heterocyclic carbine palladium compound (Pd-NHC) and 1 obtaining, 3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion joins in deionized water and dilute hydrochloric acid and dissolves, and stirs 12-24h at 40-45 ℃;
(3) reaction mixture is proceeded in tetrafluoroethylene high pressure water heating kettle, static reaction 48-72h in the baking oven of 100-110 ℃, from water heating kettle takes out, then uses deionized water and washing with alcohol, finally be placed in 50-55 ℃ of vacuum drying oven dry, obtain target catalyzer.
2. the preparation method of the imidazole salts type Cabbeen palladium catalyst with phase-transfer catalysis performance according to claim 1, is characterized in that, in step (1), and Pd (OAc)
2with the mol ratio in 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion silicon source be 1: 2-4.
3. the preparation method of the imidazole salts type Cabbeen palladium catalyst with phase-transfer catalysis performance according to claim 1, it is characterized in that, in step (2), the mol ratio of N-heterocyclic carbine palladium compound and 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion is 1: 1-8.
4. the preparation method of the imidazole salts type Cabbeen palladium catalyst with phase-transfer catalysis performance according to claim 1, is characterized in that, in step (1), the preparation method of 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion is:
Imidazole natrium is dissolved in anhydrous THF, adds 3-iodine propyl trimethoxy silicane, under argon shield, 65-70 ℃ is stirred 12-14h; After cool to room temperature, decompression is spin-dried for solvent, adds dry toluene and 3-iodine propyl trimethoxy silicane lucifuge backflow 36-48h; After reaction finishes, with dry toluene washing gained mixture, then with anhydrous methylene chloride extraction, upper solution vacuum is spin-dried for, obtains 1,3-bis-(3-trimethoxy silicon propyl group) imidazole salts iodide ion.
5. an imidazole salts type Cabbeen palladium catalyst with phase-transfer catalysis performance, is characterized in that, according to the method preparation described in claim 1-4 any one.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105289739A (en) * | 2015-11-26 | 2016-02-03 | 上海师范大学 | Imidazole PMO (Periodic Mesoporous Organosilica) supported metal type catalyst and preparation method thereof |
| CN110975939A (en) * | 2019-12-19 | 2020-04-10 | 华东师范大学 | Ethylene carbonate hydrogenation heterogeneous catalyst, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101701066A (en) * | 2009-11-11 | 2010-05-05 | 洛阳师范学院 | Polyether-loaded N-heterocyclic carbene-palladium compound and preparation method and application thereof |
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| CN101701066A (en) * | 2009-11-11 | 2010-05-05 | 洛阳师范学院 | Polyether-loaded N-heterocyclic carbene-palladium compound and preparation method and application thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105289739A (en) * | 2015-11-26 | 2016-02-03 | 上海师范大学 | Imidazole PMO (Periodic Mesoporous Organosilica) supported metal type catalyst and preparation method thereof |
| CN110975939A (en) * | 2019-12-19 | 2020-04-10 | 华东师范大学 | Ethylene carbonate hydrogenation heterogeneous catalyst, and preparation method and application thereof |
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