Cu-TBAF催化三甲氧基芳基硅烷及固载催化剂在C-C、C-N键形成反应中的研究
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摘要
由金属催化炔烃加成得到C-C键,由金属催化含氮化合物芳香化合成得到C-N键,以及在反应中金属催化剂的催化循环利用等问题在有机合成化学中均占有重要地位。本论文围绕这三个主题进行相关的有机合成研究。本论文共分二部分：1、C-N键的形成及由炔烃加成得到C-C键的合成反应。2、催化剂的催化循环利用。
第一部分综述了近年来各种金属催化的C-N键的形成反应及由炔烃加成得到C-C键的合成反应,并研究和探讨了Cu-TBAF催化三甲氧基芳基硅烷在过渡金属催化下对富电子官能团的反应：(1)在室温下,三甲氧基芳基硅烷经过催化量的TBAF、Cu(OAc)_2和P(C6F5)3催化活化后,再加入含氮化合物,经室温搅拌后得到含氮的芳烃化合物。在通过对反应的部分机理研究时发现：铜和磷配体的存在有助于实现催化量的TBAF催化舌化三甲氧基芳基硅烷。反应产率从中等到优,首次实现了在中性情况下催化量的氟源对硅烷的活化,具有操作简便、反应条件温和等优点。这改变了以往硅烷需要当量的强碱或是氟源从而实现自身的活化。这将对低毒、易制备、易储存的硅烷的工业化推广和发展提供了一条较为绿色的通道。(2)在室温下,三甲氧基芳基硅烷经过催化量的TBAF、Cu(OAc)_2和PPh3催化活化后,再加入催化量的铑、当量的炔烃化合物和水,经过加热回流搅拌后得到芳基烯烃化合物。并且我们还通过机理研究证明此加成反应中并不涉及1,4-Rh迁移。反应产率从中等到优,再次实现了在中性情况下催化量的氟源对硅烷的活化,具有操作简便、反应条件温和、产物区域选择性高等优点。
第二部分研究了在Suzuki反应中,将钯金属(?)合附着在含磷配体的固体附着物上,以磷酸钾作碱,氮气保护下,在甲苯溶剂中加热回流中得到了一系列的芳基硼酸和芳基溴化物的偶联产物。反应产率从中等到优秀,具有操作简便、反应条件温和、金属催化剂及配体可反复利用等优点。
ABSTRACT
The problem which contained of the forming of C-C bond from the metal catalyzed addition of alkynes, the forming of C-N bond from the arylation of nitrogen cotained compounds, and the reusing of the catalyst. In this paper, it focuses on these three topics of about organic synthesis research. This paper has two parts. The first part focuses on the forming of C-N bond and the forming of C-C bond from the addition of alkynes. The second (?)art focuses on the reuse of catalyst.
The first part of the paper has an overview of the various metal-catalyzed C-N bond formation reaction, and by the addition of alkynes to be C-C bond synthesis reaction in recent years. (1) Under the room tempera(?)are, the nitrogen compounds was added to the solution after the aryl trimethoxysilane was activated by catalytic amount of TBAF, Cu(OAc)_2 and P(C_6F_5)_3. The nitrogen-containing aromatic compounds were obtained through the solution was stired under room temperature. A new discovery was found when researching on the part of the mechanism of the reaction:the exist of Cu and the Phosphorus ligands can be helpful to the catalytic amount of TBAF catalyzed aryl trimethoxysilane. The silane was catalyzed by a catalytic amount of Fluoride source under neutral (?) ndition at the first time. A series of substrates were achieved with the yield from medium to good. It has many advantages like simple, mild reaction condition, etc. The low toxicity, easy preparation, easy storage of silane which will provide a more green method to be promoted of industrialization and development. (2) U (?)der the room temperature, a catalytic amount of rhodium, equivalent alkyne compounds and water were added after the trimethoxy aryl silane was catalyzed by catalytic amount of TBAF, Cu(OAc)2 and PPh_3, then stirring and reflex. A series of substrates of aryl olefin compounds were achieved with the yield from medium to good. The silane was catalyzed by a catalytic amount of fluoride source under the neutral condition again. It provides a simple, mild condition, high regional selective to synthesis the aryl olefin compounds.
The second part of the paper is about the study in the Suzuki reaction, palladium was attached to the phosphorus-containing ligand solid fixtures, providing the potassium phosphate as base, a series of aryl-boric acid and the aryl bromide coupling products were obtained with the yie(?) from medium to good after the stiring and reflexing in toluene solvent that under the protection of nitrogen. It has merits of simple operation, mild reaction conditions and metal catalyst and ligand can be used repeatedly, etc..
第一部分综述了近年来各种金属催化的C-N键的形成反应及由炔烃加成得到C-C键的合成反应,并研究和探讨了Cu-TBAF催化三甲氧基芳基硅烷在过渡金属催化下对富电子官能团的反应：(1)在室温下,三甲氧基芳基硅烷经过催化量的TBAF、Cu(OAc)_2和P(C6F5)3催化活化后,再加入含氮化合物,经室温搅拌后得到含氮的芳烃化合物。在通过对反应的部分机理研究时发现：铜和磷配体的存在有助于实现催化量的TBAF催化舌化三甲氧基芳基硅烷。反应产率从中等到优,首次实现了在中性情况下催化量的氟源对硅烷的活化,具有操作简便、反应条件温和等优点。这改变了以往硅烷需要当量的强碱或是氟源从而实现自身的活化。这将对低毒、易制备、易储存的硅烷的工业化推广和发展提供了一条较为绿色的通道。(2)在室温下,三甲氧基芳基硅烷经过催化量的TBAF、Cu(OAc)_2和PPh3催化活化后,再加入催化量的铑、当量的炔烃化合物和水,经过加热回流搅拌后得到芳基烯烃化合物。并且我们还通过机理研究证明此加成反应中并不涉及1,4-Rh迁移。反应产率从中等到优,再次实现了在中性情况下催化量的氟源对硅烷的活化,具有操作简便、反应条件温和、产物区域选择性高等优点。
第二部分研究了在Suzuki反应中,将钯金属(?)合附着在含磷配体的固体附着物上,以磷酸钾作碱,氮气保护下,在甲苯溶剂中加热回流中得到了一系列的芳基硼酸和芳基溴化物的偶联产物。反应产率从中等到优秀,具有操作简便、反应条件温和、金属催化剂及配体可反复利用等优点。
ABSTRACT
The problem which contained of the forming of C-C bond from the metal catalyzed addition of alkynes, the forming of C-N bond from the arylation of nitrogen cotained compounds, and the reusing of the catalyst. In this paper, it focuses on these three topics of about organic synthesis research. This paper has two parts. The first part focuses on the forming of C-N bond and the forming of C-C bond from the addition of alkynes. The second (?)art focuses on the reuse of catalyst.
The first part of the paper has an overview of the various metal-catalyzed C-N bond formation reaction, and by the addition of alkynes to be C-C bond synthesis reaction in recent years. (1) Under the room tempera(?)are, the nitrogen compounds was added to the solution after the aryl trimethoxysilane was activated by catalytic amount of TBAF, Cu(OAc)_2 and P(C_6F_5)_3. The nitrogen-containing aromatic compounds were obtained through the solution was stired under room temperature. A new discovery was found when researching on the part of the mechanism of the reaction:the exist of Cu and the Phosphorus ligands can be helpful to the catalytic amount of TBAF catalyzed aryl trimethoxysilane. The silane was catalyzed by a catalytic amount of Fluoride source under neutral (?) ndition at the first time. A series of substrates were achieved with the yield from medium to good. It has many advantages like simple, mild reaction condition, etc. The low toxicity, easy preparation, easy storage of silane which will provide a more green method to be promoted of industrialization and development. (2) U (?)der the room temperature, a catalytic amount of rhodium, equivalent alkyne compounds and water were added after the trimethoxy aryl silane was catalyzed by catalytic amount of TBAF, Cu(OAc)2 and PPh_3, then stirring and reflex. A series of substrates of aryl olefin compounds were achieved with the yield from medium to good. The silane was catalyzed by a catalytic amount of fluoride source under the neutral condition again. It provides a simple, mild condition, high regional selective to synthesis the aryl olefin compounds.
The second part of the paper is about the study in the Suzuki reaction, palladium was attached to the phosphorus-containing ligand solid fixtures, providing the potassium phosphate as base, a series of aryl-boric acid and the aryl bromide coupling products were obtained with the yie(?) from medium to good after the stiring and reflexing in toluene solvent that under the protection of nitrogen. It has merits of simple operation, mild reaction conditions and metal catalyst and ligand can be used repeatedly, etc..
引文
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