MCM-41负载双齿膦钯（O）配合物的合成及其在有机合成中的应用
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摘要
从工业易得的γ-氨丙基三乙氧基硅烷出发,经与MCM-41缩合固载,制得氨基功能化的MCM-41介孔材料(MCM-41-NH2),后者再与二苯膦基甲醇缩合,制备得到双膦功能化的MCM-41介孔材料(MCM-41-2P)。MCM-41-2P依次与PdCl2反应,接着用水合肼还原,首次设计合成了新型的MCM-41负载双齿膦钯(0)配合物(MCM-41-2P-Pd(0)),用XRD、XPS和元素分析等方法对其结构进行表征。
研究MCM-41-2P-Pd(0)催化芳基卤化物和共轭烯烃的Heck芳基化反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(0)存在下,芳基碘化物及带有吸电子取代基的芳基溴化物与苯乙烯、丙烯酸、丙烯酸丁酯、丙烯酰胺等共轭烯烃的芳基化反应能顺利进行,高立体选择性、高产率地生成相应的偶联产物。在催化量的MCM-41-2P-Pd(0)和三苯基膦存在下,不活泼芳基溴化物也能与共轭烯烃顺利进行偶联反应,经过较长反应时间后也能以良好的产率、高立体选择性地生成了相应的偶联产物。在催化量的MCM-41-2P-Pd(0)存在下,以哌啶为碱,CuI为助催化剂,芳基碘和各种端炔的Sonogashira偶联反应能顺利进行,高产率地生成相应的双取代乙炔。研究MCM-41-2P-Pd(0)催化芳基卤化物和芳基硼酸的Suzuki偶联反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(0)存在下,以K2CO3作为碱,二氧六环为溶剂,芳基碘化物和芳基硼酸偶联反应在80℃能顺利进行,高产率地生成联苯类化合物。芳基溴化物和芳基硼酸的偶联反应在100℃也能顺利进行,以较好的产率生成了相应的联苯类化合物。
研究MCM-41-2P-Pd(II)催化芳基卤化物和苯胺、正丁醇的Heck羰基化反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(II)存在下,各种不同的芳基碘化物都能和苯胺或正丁醇进行酰胺化或丁氧基羰基化反应,且产率较高。在催化量的MCM-41-2P-Pd(II)和三苯基膦存在下,不活泼芳基溴化物也能与苯胺或正丁醇进行酰胺化或丁氧基羰基化反应。研究MCM-41-2P-Pd(0)催化芳基碘化物和端炔的羰基化Sonogashira偶联反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(0)存在下,在室温、CO(1 atm)条件下,以Et3N作为碱,含供电性子取代基的碘代芳烃与各种端炔的羰基化Sonogashira偶联反应能顺利进行,且产率较高。以NH3作为碱,THF为溶剂,含吸电子取代基的碘代芳烃仅能与苯乙炔进行羰基化Sonogashira偶联反应,且产率较低。该新型负载钯催化剂在上述反应中均易与产物分离,回收利用多次后其活性基本不变。
Diphosphino-functionalized MCM-41 anchored palladium(0) complex (denoted as MCM-41-2P-Pd(0)) was conveniently synthesized from commercially available and cheapγ-aminopropyltriethoxysilane via immobilization on MCM-41, followed by reacting with diphenylphosphinomethanol and palladium chloride, then the reduction with hydrazine hydrate. This palladium complex was characterized by XRD, XPS and elemental analysis.
The Heck arylation reaction of styrene, acrylic acid, butyl acrylate, acrylamide with aryl iodides or electron-deficient aryl bromides proceeded very smoothly in the presence of MCM-41-2P-Pd(0) complex to give the corresponding arylation products in excellent yields. Although the reactivity of unactivated aryl bromides was low under the same conditions, the arylation reaction could also take place in the presence of a catalytic amounts of MCM-41-2P-Pd(0) and PPh3 giving the corresponding arylation products in good yields.
In order to evaluate the catalytic activity of MCM-41-2P-Pd(0), the Sonogashira reactions of terminal alkynes with aryl iodides were studied.The Sonogashira reactions proceeded smoothly in the presence of a catalytic amounts of MCM-41-2P-Pd(0) and CuI in piperidine at room temperature giving the corresponding coupling products in excellent yields. The Suzuki reactions of arylboronic acids with aryl halides were also studied. The Suzuki reactions of a variety of substituted iodobenzene with arylboronic acids were carried out with a catalytic amounts of MCM-41-2P-Pd(0) using K2CO3 as base in dioxane at 80℃and the reactions proceeded smoothly giving the correspond- ing coupling products in excellent yields. The Suzuki reactions of a variety of aryl bromides with arylboronic acids could also proceed smoothly at 100℃to give the corresponding coupling products in high yields on longer times.
The catalytic properties of MCM-41-2P-Pd(II) for Heck carbonylation of aryl halides were studied. The Heck carbonylation reactions of a variety of substituted iodobenzene with aniline or butanol were carried out with a catalytic amounts of MCM-41-2P-Pd(II) and the reactions proceeded smoothly giving the corresponding coupling products in high yields. Although the reactivity of unactivated aryl bromides was low under the same conditions, the arylation reaction could also take place in the presence of a catalytic amounts of MCM-41-2P-Pd(0) and PPh3 giving the correspon- ding Heck carbonylation products in good yields.
The catalytic properties of MCM-41-2P-Pd(0) for carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes and CO were studied. The carbonylative Sonogashira coupling reaction of terminal alkynes with a variety of aryl iodides with electron-donating substituents in the presence of a catalytic amounts of MCM-41-2P-Pd(0), Et3N as base and CO(1 atm) gives the corresponding alkynyl ketone in good isolated yields after stirring at room temperature for 30-72h. The carbonylative Sonogashira coupling reaction of phenylacetylene with a variety of aryl iodides with electron-withdrawing substituents was slow in the presence of a catalytic amounts of MCM-41-2P-Pd(0) in THF using ammonia water as base at room temper- ature, affording the corresponding coupling products in lower yields on longer times.
The novel MCM-41-supported bidentate phosphine palladium(0) complex catalyst can be easily recovered by simple filtration and can be reused many times without loss of activity.
研究MCM-41-2P-Pd(0)催化芳基卤化物和共轭烯烃的Heck芳基化反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(0)存在下,芳基碘化物及带有吸电子取代基的芳基溴化物与苯乙烯、丙烯酸、丙烯酸丁酯、丙烯酰胺等共轭烯烃的芳基化反应能顺利进行,高立体选择性、高产率地生成相应的偶联产物。在催化量的MCM-41-2P-Pd(0)和三苯基膦存在下,不活泼芳基溴化物也能与共轭烯烃顺利进行偶联反应,经过较长反应时间后也能以良好的产率、高立体选择性地生成了相应的偶联产物。在催化量的MCM-41-2P-Pd(0)存在下,以哌啶为碱,CuI为助催化剂,芳基碘和各种端炔的Sonogashira偶联反应能顺利进行,高产率地生成相应的双取代乙炔。研究MCM-41-2P-Pd(0)催化芳基卤化物和芳基硼酸的Suzuki偶联反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(0)存在下,以K2CO3作为碱,二氧六环为溶剂,芳基碘化物和芳基硼酸偶联反应在80℃能顺利进行,高产率地生成联苯类化合物。芳基溴化物和芳基硼酸的偶联反应在100℃也能顺利进行,以较好的产率生成了相应的联苯类化合物。
研究MCM-41-2P-Pd(II)催化芳基卤化物和苯胺、正丁醇的Heck羰基化反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(II)存在下,各种不同的芳基碘化物都能和苯胺或正丁醇进行酰胺化或丁氧基羰基化反应,且产率较高。在催化量的MCM-41-2P-Pd(II)和三苯基膦存在下,不活泼芳基溴化物也能与苯胺或正丁醇进行酰胺化或丁氧基羰基化反应。研究MCM-41-2P-Pd(0)催化芳基碘化物和端炔的羰基化Sonogashira偶联反应性能。研究结果表明,在催化量的MCM-41-2P-Pd(0)存在下,在室温、CO(1 atm)条件下,以Et3N作为碱,含供电性子取代基的碘代芳烃与各种端炔的羰基化Sonogashira偶联反应能顺利进行,且产率较高。以NH3作为碱,THF为溶剂,含吸电子取代基的碘代芳烃仅能与苯乙炔进行羰基化Sonogashira偶联反应,且产率较低。该新型负载钯催化剂在上述反应中均易与产物分离,回收利用多次后其活性基本不变。
Diphosphino-functionalized MCM-41 anchored palladium(0) complex (denoted as MCM-41-2P-Pd(0)) was conveniently synthesized from commercially available and cheapγ-aminopropyltriethoxysilane via immobilization on MCM-41, followed by reacting with diphenylphosphinomethanol and palladium chloride, then the reduction with hydrazine hydrate. This palladium complex was characterized by XRD, XPS and elemental analysis.
The Heck arylation reaction of styrene, acrylic acid, butyl acrylate, acrylamide with aryl iodides or electron-deficient aryl bromides proceeded very smoothly in the presence of MCM-41-2P-Pd(0) complex to give the corresponding arylation products in excellent yields. Although the reactivity of unactivated aryl bromides was low under the same conditions, the arylation reaction could also take place in the presence of a catalytic amounts of MCM-41-2P-Pd(0) and PPh3 giving the corresponding arylation products in good yields.
In order to evaluate the catalytic activity of MCM-41-2P-Pd(0), the Sonogashira reactions of terminal alkynes with aryl iodides were studied.The Sonogashira reactions proceeded smoothly in the presence of a catalytic amounts of MCM-41-2P-Pd(0) and CuI in piperidine at room temperature giving the corresponding coupling products in excellent yields. The Suzuki reactions of arylboronic acids with aryl halides were also studied. The Suzuki reactions of a variety of substituted iodobenzene with arylboronic acids were carried out with a catalytic amounts of MCM-41-2P-Pd(0) using K2CO3 as base in dioxane at 80℃and the reactions proceeded smoothly giving the correspond- ing coupling products in excellent yields. The Suzuki reactions of a variety of aryl bromides with arylboronic acids could also proceed smoothly at 100℃to give the corresponding coupling products in high yields on longer times.
The catalytic properties of MCM-41-2P-Pd(II) for Heck carbonylation of aryl halides were studied. The Heck carbonylation reactions of a variety of substituted iodobenzene with aniline or butanol were carried out with a catalytic amounts of MCM-41-2P-Pd(II) and the reactions proceeded smoothly giving the corresponding coupling products in high yields. Although the reactivity of unactivated aryl bromides was low under the same conditions, the arylation reaction could also take place in the presence of a catalytic amounts of MCM-41-2P-Pd(0) and PPh3 giving the correspon- ding Heck carbonylation products in good yields.
The catalytic properties of MCM-41-2P-Pd(0) for carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes and CO were studied. The carbonylative Sonogashira coupling reaction of terminal alkynes with a variety of aryl iodides with electron-donating substituents in the presence of a catalytic amounts of MCM-41-2P-Pd(0), Et3N as base and CO(1 atm) gives the corresponding alkynyl ketone in good isolated yields after stirring at room temperature for 30-72h. The carbonylative Sonogashira coupling reaction of phenylacetylene with a variety of aryl iodides with electron-withdrawing substituents was slow in the presence of a catalytic amounts of MCM-41-2P-Pd(0) in THF using ammonia water as base at room temper- ature, affording the corresponding coupling products in lower yields on longer times.
The novel MCM-41-supported bidentate phosphine palladium(0) complex catalyst can be easily recovered by simple filtration and can be reused many times without loss of activity.
引文
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