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A kind of adamantane supported nhc-pd catalyst and its preparation method and application
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A technology of adamantane and catalyst, which is applied in the field of adamantane-supported NHC-Pd catalyst and its preparation and application, can solve the problems of difficult separation of reaction products and non-reusable catalyst, and achieve simple and feasible reaction route, excellent catalytic effect, and solution The effect of recycling
Inactive Publication Date: 2017-06-16
HUBEI UNIV
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Palladium complexes, as an important representative in organometallic chemistry, can be used to catalyze coupling reactions to solve the problems of difficult separation of reaction products and non-reusable catalysts caused by traditional homogeneous catalytic systems.
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Embodiment 1-4
[0026] Example 1-4: Preparation method of adamantane-supported NHC-Pd catalyst.
[0027]
Embodiment 1
[0029] Compound 2 (0.8 g, 1.1 mmol) was dissolved in chloroform (15 mL), methyl iodide (1.37 mL, 22 mmol) was added, and the reaction was carried out at 40 °C for 24 h, a solid was precipitated, centrifuged, and the precipitate was dried to obtain compound 3 as a pale yellow solid ( 0.98 g, 70%). m.p.>300 ℃; IR(KBr): υ 3429, 3064, 1572, 1550, 1363, 1219, 1207, 835, 783 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ): δ 2.25 (s, 12H), 3.97 (s, 12H), 7.94-7.79 (m, 12H), 8.32 (s, 4H), 9.81 (s, 4H); 13 C NMR (150 MHz, DMSO-d 6 ): δ 36.2, 39.3, 45.5, 120.9, 121.4, 124.4, 127.3, 132.7, 135.7, 150.9.
Embodiment 2
[0031] Compound 2 (0.8 g, 1.1 mmol) was dissolved in dichloromethane (15 mL), methyl iodide (4.11 mL, 66 mmol) was added, and the reaction was carried out at 20 °C for 96 h, a solid was precipitated, centrifuged, and the precipitate was dried to obtain compound 3 as a pale yellow solid ( 1.30 g, 93%). m.p.>300 ℃; IR(KBr): υ 3429, 3064, 1572, 1550, 1363, 1219, 1207, 835, 783 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ): δ 2.25 (s, 12H), 3.97 (s, 12H), 7.94-7.79 (m, 12H), 8.32 (s, 4H), 9.81 (s, 4H); 13 C NMR (150 MHz, DMSO-d 6 ): δ 36.2, 39.3, 45.5, 120.9, 121.4, 124.4, 127.3, 132.7, 135.7, 150.9.
[0032]
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Abstract
The invention relates to an NHC-Pd catalyst supported by adamantine and a preparation method and application of the NHC-Pd catalyst. The three-dimensional porous NHC-Pd catalyst supported by adamantine is prepared by using 1,3,5,7-tetra(4-(1-imidazole)phenyl)adamantine as the raw material and coordinating the raw material with palladium acetate[Pd(OAc)2] after quaternization is conducted on the raw material. The catalyst has the advantages that the catalyst has high thermal stability and a certain porous property; the catalyst can be used for catalyzing a Suzuki-Miyaura coupling reaction under the mild aerobic condition and achieves the excellent catalytic effect; the catalyst can be repeatedly used through simple centrifuging and filtering after the catalytic reaction is completed, and the purpose that the homogeneous catalyst is recovered and repeatedly used is achieved; the method is simple and feasible in reaction route, and can be used as the efficient catalyst for synthesizing medicine, pesticide, perfume and functional materials.
Description
technical field [0001] The present invention relates to a porous adamantane supported NHC-Pd catalyst and its preparation method and application. Background technique [0002] The core of metal-organic chemistry, transition metal complexes, has a wide range of applications in environmental protection, new energy, materials, human health, etc. due to its advantages of high selectivity, high activity, and stability. [0003] Since the first stable, free crystalline N-heterocyclic carbene-imidazole-2-carbene-3 was isolated by Arduengo in 1991, N-heterocyclic carbene (NHC) has aroused great interest among researchers and has become the One of the hot spots in organic synthesis research. In addition to N-heterocyclic carbene, it can be used as benzoin condensation and nucleophilic substitution reaction, Stetter reaction, aldehyde oxidation catalytic reaction, α, β-unsaturated aldehyde to form homoenolate reaction with various electrophiles, aldehyde and amide reaction Coupling ...
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