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NHC-Pd catalyst supported by adamantine and preparation method and application of NHC-Pd catalyst
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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, which can solve the problems of difficult separation of reaction products and non-reusable catalyst, and achieve simple and feasible reaction route, excellent catalytic effect, high heat The effect of stability
Inactive Publication Date: 2016-02-17
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 (0.8g, 1.1mmol) was dissolved in chloroform (15mL), added iodomethane (1.37mL, 22mmol), reacted at 40°C for 24h, a solid precipitated, centrifuged, precipitated and dried to obtain a light yellow solid compound 3 (0.98g, 70%). m.p.>300℃;IR(KBr): υ 3429,3064,1572,1550,1363,1219,1207,835,783cm -1 ; 1 HNMR (400MHz, 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 CNMR (150MHz, 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 (0.8g, 1.1mmol) was dissolved in dichloromethane (15mL), added iodomethane (4.11mL, 66mmol), reacted at 20°C for 96h, a solid precipitated, centrifuged, precipitated and dried to obtain a light yellow solid compound 3 (1.30g, 93%). m.p.>300℃;IR(KBr): υ 3429,3064,1572,1550,1363,1219,1207,835,783cm -1 ; 1 HNMR (400MHz, 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 CNMR (150MHz, 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 invention relates to a porous adamantane-supported NHC-Pd catalyst, a preparation method and application thereof. Background technique [0002] Transition metal complexes, the core of organometallic chemistry, have a wide range of applications in environmental protection, new energy, materials, and human health due to their high selectivity, high activity, and stability. [0003] Since Arduengo isolated the first stable, free crystalline N-heterocyclic carbene-imidazole-2-carbene-3 in 1991, N-heterocyclic carbene (NHC) has attracted great interest from researchers and has become a One of the hotspots of organic synthesis research. N-heterocyclic carbene can be used as benzoin condensation and nucleophilic substitution reaction, Stetter reaction, oxidation catalytic reaction of aldehyde, reaction of α, β-unsaturated aldehyde to form homoenolate and various electrophiles, and reaction between aldehyde and amideCoupling reaction, CO 2 The catalyst...
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