在聚乙二醇中钯催化的偶联反应
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摘要
绿色化学是指在制造化学产品时应有效利用原料,消除废物和避免使用有毒的和危险的试剂。绿色化学又称“环境友好化学”或“清洁化学”。目前世界上很多国家已把“绿色化学”作为新世纪化学发展的方向之一。
聚乙二醇(PEG)是一种应用越来越广泛的绿色溶剂,在合成化学和非均相催化方面得到了越来越多的关注。聚乙二醇(PEG)在室温和高温条件下的粘性,使它可以应用于很多的化学反应。近几年,聚乙二醇(PEG)作为有机合成反应中的绿色溶剂有其独特的性质,如:低毒性、热稳定性、价格低廉、无挥发等。许多有机合成反应使用聚乙二醇(PEG)为溶剂,如:Heck反应、Suzuki偶联反应、氧化反应、还原反应、加成反应和不对称aldo反应等。目前,已经有文章报道了聚乙二醇(PEG)是可以重复使用的溶剂。聚乙二醇(PEG)在生物学方面的应用较广泛,如药物学和诊断学方面等,也将会越来越多的应用于有机合成化学。低分子量的液态聚乙二醇(PEG)作为溶剂时可以与水互溶,也可以不加入水。聚乙二醇(PEG)在高温150-200℃或酸碱性条件下都是稳定的。已经有文章报道聚乙二醇(PEG)在无机盐中作为配体溶剂时可以增加阴离子的活性,而且利用聚乙二醇(PEG)独特的物理、化学特性去进行反应,可以得到较高的产率,这些是其他有机溶剂达不到的。聚乙二醇(PEG)作为有机绿色溶剂在有机合成化学中已经引起了很大的关注。
使用绿色环保的反应介质是绿色化学的要求,也是有机合成化学的发展方向之一。以这些内容为目标,本文研究的反应以聚乙二醇(PEG)-600为反应溶剂,这样大大减少了对环境的污染,而且可以重复使用。我们成功的利用聚乙二醇(PEG)-600作为反应溶剂在钯作为催化剂的条件下合成了苯基磷酸酯和苯基硼酸酯化合物。合成方法操作简单一锅反应,适用底物范围广。同时采用IR、1HNMR和13CNMR对部分化合物进行了结构表征。
含有C-P键的磷化合物在自然界中是不常见的。它们多种多样的生物活性,在很长一段时间里已经引起了有机合成化学和药理学的兴趣。苯基磷酸酯和它的衍生物是一类非常重要的化合物,主要应用于药学、有机合成和高分子化学。含有芳基磷酸酯的化合物大部分应用于设计燃料细胞膜、专门光学材料和合成杂环化合物等。最近,人们对含磷化合物在药物化学和核酸化学方面的兴趣日渐增长,因为核酸化学方面存在生物活性,含磷化合物有C-P键可以形成很多具有生物活性的有机化合物。本文研究了在钯作催化剂、PEG-600为溶剂、温度130℃和三乙胺为碱的条件下卤苯与亚磷酸二乙酯反应合成了苯基磷酸酯。
芳基硼酸和它的酯类是具有许多功能的中间体,应用它们独特的性质可以去形成C-C键、C-N键和C-O键。而且,由于它们的稳定性和低毒性,人们把研究热点放在了分子识别和药物方面的应用。芳基硼酸和它的酯类已经越来越多的应用在有机合成和药物治疗方面。在生物学、医学或材料学上,芳基硼酸酯已被用于烃类的传感器、核苷和酶的抑制剂,还可以在某些脑瘤病人的治疗法中用作治疗剂等。此外苯硼酸还可制成测定糖类的传感器。本文研究了钯作催化剂、PEG-600为溶剂、温度90℃和醋酸钠为碱的条件下卤苯与联硼酸频那醇酯反应合成了苯基硼酸酯。
上述的两类化合物是重要的含有C-P键和C-B键的物质,在有机合成化学中具有重要的作用。因此研究含C-P键和C-B键化合物的合成方法具有重要的意义。而随着环境科学的发展迫切要求人们发展绿色环保条件下的有机合成方法。本课题在总结前人工作的基础上,研究了聚乙二醇(PEG)-600在有机合成中的应用。此项工作以聚乙二醇(PEG)-600作溶剂,钯作催化剂合成了苯基磷酸酯和苯基硼酸酯。本课题中的合成方法操作简便、溶剂无毒和可以回收利用,这一新方法符合绿色环保的要求,将会促进绿色化学的发展。
Green chemistry is to point to in manufacturing chemical products that should be effective used of raw material, eliminated waste and avoided using toxic and dangerous reagents. Green chemistry also says "environmentally friendly chemistry" or "clean chemistry". At present many countries of the world have already put "Green Chemistry" as one of the direction of chemical development in the new century.
Polyethylene Gglycol (PEG) has been emerging as a promising green solvent and receiving more attention for both combinatorialas well as for heterogeneous catalysts. The viscosity of PEG at ambient and higher temperatures gives them significant advantage to use for all general operations. In recent years, PEG has emerged as alternative green reaction medium with unique properties such as low toxicity, thermal stability, inexpensive and nonvolatile. Many organic reactions have been carried out using PEG as solvent or co-solvent, such as Heck reaction, Suzuki-Miyaura cross-coupling reaction, oxidation, reduction, addition, and asymmetric aldo reaction. The use of PEG as a recyclable solvent system has also been reported. PEG is a biologically acceptable polymer which has been used extensively in drug delivery and in bioconjugates as tools for diagnostics. It is also being extensively used in organic substrates. Lower-molecular weight liquid PEGs can be used as solvents with or without addition of water. PEGs are stable at high temperatures up to 150-200℃and show higher stability in acidic and basic conditions. It has previously been suggested that PEGs could be used as complexing solvents of inorganic salts, in order to enhance the reactivity of the anion with the organic substrate. In these systems, the anion could be brought into solution with higher reactivity. Additionally, it may be possible by utilizing the unique physicochemical properties of PEGs to realize reactivity and/or selectivity that cannot be attained in organic solvents. The use of PEG as a reaction solvent has received considerable attention in synthetic organic chemistry.
Using green reaction media is green chemistry demand, and is also one of the development directions of organic synthesis chemistry. With these content as the goal, this paper studies reaction with polyethylene glycol (PEG)-600 for solvent, so that greatly reduces the pollution to the environment and can be reused. We successfully used polyethylene glycol (PEG)-600 as solvent and palladium as a catalyst in the synthesis of phenyl phosphate and phenyl boric acid ester compounds under the conditions. This method is suitable for operaction and experimental simplicity and various substrates. Most of compounds were characterized by IR, 1HNMR and 13CNMR.
Phosphorus compounds containing the C-P bond are not particularly abundant in nature. Their diverse biological activities have for a long time attracted considerable interest of synthetic and pharmacological. Arylphosphonates and their derivatives are important classes of compounds with applications in medicinal, organic, and polymer chemistries. Compounds containing arylphosphonate moieties are used in designing fuel cell membranes, materials with special optical properties and in the synthesis of heterocyclic compounds. In recent years there has been a growing interest in these classes of phosphorus compounds in medicinal chemistry and nucleic acid chemistry due to biological activity that the presence of a C-P bond can confer to many organic compounds. This work with palladium as catalysts, polyethylene glycol (PEG)-600 as solvent, temperature at 130℃, Et3N as alkali, Halogen benzenes and diethyl phosphite synthesize phenyl phosphates.
Arylboronic acids and their esters are versatile intermediates in organic synthesis to construct carbon-carbon, carbon-nitrogen and carbon-oxygen bonds due to their unique reactivity and air stability. In addition, attention has recently also been paid to their applications in molecular recognition and pharmaceutical candidates owing to their high stability and low toxicity. Arylboronic acids and their esters have found increasing application in organic synthesis and medical treatments. In biology, medicine or materials science, aryl boronic esters have been used for hydrocarbon sensors, nucleosides and enzyme inhibitors, but also in some brain tumor patients in therapy for the treatment agent. Besides determination of phenylboronic acid can also be made of sugar sensor. This work with palladium as catalysts, polyethylene glycol (PEG)-600 as solvent, temperature at 90℃, NaNO2 as alkali, Halogen benzenes and B2pin2 synthesize phenyl boric acid ester compounds.
The above two kinds of compounds are important containing C-P bond and C-B key materials, and playing an important role in organic synthetic chemistry. Therefore, the research synthesis method of containing C-P bond and C-B key compounds has the vital significance. With the development of environmental science urgently requires people to develop green environmental conditions of organic synthesis method. This topic in concluded on the basis of previous work, studies the polyethylene glycol (PEG)-600 applications in organic synthesis. This work with polyethylene glycol (PEG)-600 as solvent, palladium as catalysts synthesizes phenyl phosphate and phenyl boric acid ester compounds. This topic in the synthesis method is easy to operate, solvent non-toxic, can recycling. This new method with green environmental protection, will promote the development of green chemistry.
聚乙二醇(PEG)是一种应用越来越广泛的绿色溶剂,在合成化学和非均相催化方面得到了越来越多的关注。聚乙二醇(PEG)在室温和高温条件下的粘性,使它可以应用于很多的化学反应。近几年,聚乙二醇(PEG)作为有机合成反应中的绿色溶剂有其独特的性质,如:低毒性、热稳定性、价格低廉、无挥发等。许多有机合成反应使用聚乙二醇(PEG)为溶剂,如:Heck反应、Suzuki偶联反应、氧化反应、还原反应、加成反应和不对称aldo反应等。目前,已经有文章报道了聚乙二醇(PEG)是可以重复使用的溶剂。聚乙二醇(PEG)在生物学方面的应用较广泛,如药物学和诊断学方面等,也将会越来越多的应用于有机合成化学。低分子量的液态聚乙二醇(PEG)作为溶剂时可以与水互溶,也可以不加入水。聚乙二醇(PEG)在高温150-200℃或酸碱性条件下都是稳定的。已经有文章报道聚乙二醇(PEG)在无机盐中作为配体溶剂时可以增加阴离子的活性,而且利用聚乙二醇(PEG)独特的物理、化学特性去进行反应,可以得到较高的产率,这些是其他有机溶剂达不到的。聚乙二醇(PEG)作为有机绿色溶剂在有机合成化学中已经引起了很大的关注。
使用绿色环保的反应介质是绿色化学的要求,也是有机合成化学的发展方向之一。以这些内容为目标,本文研究的反应以聚乙二醇(PEG)-600为反应溶剂,这样大大减少了对环境的污染,而且可以重复使用。我们成功的利用聚乙二醇(PEG)-600作为反应溶剂在钯作为催化剂的条件下合成了苯基磷酸酯和苯基硼酸酯化合物。合成方法操作简单一锅反应,适用底物范围广。同时采用IR、1HNMR和13CNMR对部分化合物进行了结构表征。
含有C-P键的磷化合物在自然界中是不常见的。它们多种多样的生物活性,在很长一段时间里已经引起了有机合成化学和药理学的兴趣。苯基磷酸酯和它的衍生物是一类非常重要的化合物,主要应用于药学、有机合成和高分子化学。含有芳基磷酸酯的化合物大部分应用于设计燃料细胞膜、专门光学材料和合成杂环化合物等。最近,人们对含磷化合物在药物化学和核酸化学方面的兴趣日渐增长,因为核酸化学方面存在生物活性,含磷化合物有C-P键可以形成很多具有生物活性的有机化合物。本文研究了在钯作催化剂、PEG-600为溶剂、温度130℃和三乙胺为碱的条件下卤苯与亚磷酸二乙酯反应合成了苯基磷酸酯。
芳基硼酸和它的酯类是具有许多功能的中间体,应用它们独特的性质可以去形成C-C键、C-N键和C-O键。而且,由于它们的稳定性和低毒性,人们把研究热点放在了分子识别和药物方面的应用。芳基硼酸和它的酯类已经越来越多的应用在有机合成和药物治疗方面。在生物学、医学或材料学上,芳基硼酸酯已被用于烃类的传感器、核苷和酶的抑制剂,还可以在某些脑瘤病人的治疗法中用作治疗剂等。此外苯硼酸还可制成测定糖类的传感器。本文研究了钯作催化剂、PEG-600为溶剂、温度90℃和醋酸钠为碱的条件下卤苯与联硼酸频那醇酯反应合成了苯基硼酸酯。
上述的两类化合物是重要的含有C-P键和C-B键的物质,在有机合成化学中具有重要的作用。因此研究含C-P键和C-B键化合物的合成方法具有重要的意义。而随着环境科学的发展迫切要求人们发展绿色环保条件下的有机合成方法。本课题在总结前人工作的基础上,研究了聚乙二醇(PEG)-600在有机合成中的应用。此项工作以聚乙二醇(PEG)-600作溶剂,钯作催化剂合成了苯基磷酸酯和苯基硼酸酯。本课题中的合成方法操作简便、溶剂无毒和可以回收利用,这一新方法符合绿色环保的要求,将会促进绿色化学的发展。
Green chemistry is to point to in manufacturing chemical products that should be effective used of raw material, eliminated waste and avoided using toxic and dangerous reagents. Green chemistry also says "environmentally friendly chemistry" or "clean chemistry". At present many countries of the world have already put "Green Chemistry" as one of the direction of chemical development in the new century.
Polyethylene Gglycol (PEG) has been emerging as a promising green solvent and receiving more attention for both combinatorialas well as for heterogeneous catalysts. The viscosity of PEG at ambient and higher temperatures gives them significant advantage to use for all general operations. In recent years, PEG has emerged as alternative green reaction medium with unique properties such as low toxicity, thermal stability, inexpensive and nonvolatile. Many organic reactions have been carried out using PEG as solvent or co-solvent, such as Heck reaction, Suzuki-Miyaura cross-coupling reaction, oxidation, reduction, addition, and asymmetric aldo reaction. The use of PEG as a recyclable solvent system has also been reported. PEG is a biologically acceptable polymer which has been used extensively in drug delivery and in bioconjugates as tools for diagnostics. It is also being extensively used in organic substrates. Lower-molecular weight liquid PEGs can be used as solvents with or without addition of water. PEGs are stable at high temperatures up to 150-200℃and show higher stability in acidic and basic conditions. It has previously been suggested that PEGs could be used as complexing solvents of inorganic salts, in order to enhance the reactivity of the anion with the organic substrate. In these systems, the anion could be brought into solution with higher reactivity. Additionally, it may be possible by utilizing the unique physicochemical properties of PEGs to realize reactivity and/or selectivity that cannot be attained in organic solvents. The use of PEG as a reaction solvent has received considerable attention in synthetic organic chemistry.
Using green reaction media is green chemistry demand, and is also one of the development directions of organic synthesis chemistry. With these content as the goal, this paper studies reaction with polyethylene glycol (PEG)-600 for solvent, so that greatly reduces the pollution to the environment and can be reused. We successfully used polyethylene glycol (PEG)-600 as solvent and palladium as a catalyst in the synthesis of phenyl phosphate and phenyl boric acid ester compounds under the conditions. This method is suitable for operaction and experimental simplicity and various substrates. Most of compounds were characterized by IR, 1HNMR and 13CNMR.
Phosphorus compounds containing the C-P bond are not particularly abundant in nature. Their diverse biological activities have for a long time attracted considerable interest of synthetic and pharmacological. Arylphosphonates and their derivatives are important classes of compounds with applications in medicinal, organic, and polymer chemistries. Compounds containing arylphosphonate moieties are used in designing fuel cell membranes, materials with special optical properties and in the synthesis of heterocyclic compounds. In recent years there has been a growing interest in these classes of phosphorus compounds in medicinal chemistry and nucleic acid chemistry due to biological activity that the presence of a C-P bond can confer to many organic compounds. This work with palladium as catalysts, polyethylene glycol (PEG)-600 as solvent, temperature at 130℃, Et3N as alkali, Halogen benzenes and diethyl phosphite synthesize phenyl phosphates.
Arylboronic acids and their esters are versatile intermediates in organic synthesis to construct carbon-carbon, carbon-nitrogen and carbon-oxygen bonds due to their unique reactivity and air stability. In addition, attention has recently also been paid to their applications in molecular recognition and pharmaceutical candidates owing to their high stability and low toxicity. Arylboronic acids and their esters have found increasing application in organic synthesis and medical treatments. In biology, medicine or materials science, aryl boronic esters have been used for hydrocarbon sensors, nucleosides and enzyme inhibitors, but also in some brain tumor patients in therapy for the treatment agent. Besides determination of phenylboronic acid can also be made of sugar sensor. This work with palladium as catalysts, polyethylene glycol (PEG)-600 as solvent, temperature at 90℃, NaNO2 as alkali, Halogen benzenes and B2pin2 synthesize phenyl boric acid ester compounds.
The above two kinds of compounds are important containing C-P bond and C-B key materials, and playing an important role in organic synthetic chemistry. Therefore, the research synthesis method of containing C-P bond and C-B key compounds has the vital significance. With the development of environmental science urgently requires people to develop green environmental conditions of organic synthesis method. This topic in concluded on the basis of previous work, studies the polyethylene glycol (PEG)-600 applications in organic synthesis. This work with polyethylene glycol (PEG)-600 as solvent, palladium as catalysts synthesizes phenyl phosphate and phenyl boric acid ester compounds. This topic in the synthesis method is easy to operate, solvent non-toxic, can recycling. This new method with green environmental protection, will promote the development of green chemistry.
引文
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