MCM-41负载双齿氮钯配合物催化的碳—碳偶联反应研究
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摘要
从3-(2-氨乙基氨基)丙基三甲氧基硅烷出发,经与MCM-41缩合固载,用三甲基氯硅烷硅化后制备了双氮功能化的MCM-41介孔材料(MCM-41-2N)。后者再与Pd(OAc)_2反应,合成了MCM-41负载双齿氮钯(Ⅱ)配合物[MCM-41-2N- Pd(OAc)_2]。
研究了MCM-41-2N-Pd(OAc)_2催化芳酰氯和端炔的交叉偶联反应性能。研究结果表明,在催化量的MCM-41-2N-Pd(Ⅱ)配合物和CuI存在下,酰氯和端炔能顺利进行交叉偶联反应,高产率地合成炔酮。该新型负载钯催化剂易与产物分离,回收利用多次后其活性基本不变。
研究了MCM-41-2N-Pd(OAc)_2催化芳酰氯、端炔和肼之间的交叉偶联/缩合串联反应,提供了“一锅法”合成吡唑类化合物的新途径。MCM-41负载双齿氮钯(Ⅱ)配合物还能有效地催化芳酰氯与芳基铋,芳基碘与芳基铋的交叉偶联反应,较高产率地生成相应的偶联产物,分别为二芳酮、联苯类化合物的合成提供了绿色新途径。通过回收实验发现该负载型双齿氮钯(Ⅱ)配合物催化剂具有良好的回收再利用性能。
An MCM-41-supported bidentate nitrogen palladium(Ⅱ) complex [MCM-41- 2N-Pd(OAc)_2] was prepared from 3-(2-aminoethylamino)propyltrimethoxysilane via immobilization on MCM-41, followed by reacting with palladium acetate.
In order to evaluate the catalytic activity of MCM-41-2N-Pd(OAc)_2, we studied cross-coupling reaction of acyl chlorides and terminal alkynes catalyzed by MCM-41-2N-Pd(OAc)_2 for the formation of ynones. The results showed that reactions proceeded very smoothly in the presence of a catalytic of MCM-41-2N-Pd(OAc)_2 and CuI, giving the corresponding coupled products in good to high yields. This novel supported palladium catalyst can be easily recovered by simple filtration and reused many times without loss of activity.
We also studied tandem cross-coupling/condensation reaction of acyl chlorides, terminal alkynes and hydrazine catalyzed by MCM-41-2N-Pd(OAc)_2, providing a novel one-pot method for the preparation of pyrazoles. It was founded that the MCM-41-2N-Pd(OAc)_2 exhibits high catalytic activity in both the reaction of acyl chlorides with arylbismuths and the reaction of aryl iodides with arylbismuths, giving the corresponding coupled products in good to high yields, providing a green procedure for the synthesis of diaryl ketones and biaryls, respectively. The novel supported bidentate nitrogen palladium catalyst can be easily recovered by simple filtration and reused many times without loss of activity.
研究了MCM-41-2N-Pd(OAc)_2催化芳酰氯和端炔的交叉偶联反应性能。研究结果表明,在催化量的MCM-41-2N-Pd(Ⅱ)配合物和CuI存在下,酰氯和端炔能顺利进行交叉偶联反应,高产率地合成炔酮。该新型负载钯催化剂易与产物分离,回收利用多次后其活性基本不变。
研究了MCM-41-2N-Pd(OAc)_2催化芳酰氯、端炔和肼之间的交叉偶联/缩合串联反应,提供了“一锅法”合成吡唑类化合物的新途径。MCM-41负载双齿氮钯(Ⅱ)配合物还能有效地催化芳酰氯与芳基铋,芳基碘与芳基铋的交叉偶联反应,较高产率地生成相应的偶联产物,分别为二芳酮、联苯类化合物的合成提供了绿色新途径。通过回收实验发现该负载型双齿氮钯(Ⅱ)配合物催化剂具有良好的回收再利用性能。
An MCM-41-supported bidentate nitrogen palladium(Ⅱ) complex [MCM-41- 2N-Pd(OAc)_2] was prepared from 3-(2-aminoethylamino)propyltrimethoxysilane via immobilization on MCM-41, followed by reacting with palladium acetate.
In order to evaluate the catalytic activity of MCM-41-2N-Pd(OAc)_2, we studied cross-coupling reaction of acyl chlorides and terminal alkynes catalyzed by MCM-41-2N-Pd(OAc)_2 for the formation of ynones. The results showed that reactions proceeded very smoothly in the presence of a catalytic of MCM-41-2N-Pd(OAc)_2 and CuI, giving the corresponding coupled products in good to high yields. This novel supported palladium catalyst can be easily recovered by simple filtration and reused many times without loss of activity.
We also studied tandem cross-coupling/condensation reaction of acyl chlorides, terminal alkynes and hydrazine catalyzed by MCM-41-2N-Pd(OAc)_2, providing a novel one-pot method for the preparation of pyrazoles. It was founded that the MCM-41-2N-Pd(OAc)_2 exhibits high catalytic activity in both the reaction of acyl chlorides with arylbismuths and the reaction of aryl iodides with arylbismuths, giving the corresponding coupled products in good to high yields, providing a green procedure for the synthesis of diaryl ketones and biaryls, respectively. The novel supported bidentate nitrogen palladium catalyst can be easily recovered by simple filtration and reused many times without loss of activity.
引文
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