芳基取代烯烃的三重选择性绿色双氧化反应研究
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摘要
本文报道了一种新型的将芳基取代烯烃转化为芳基取代的乙二醇单酯的选择性顺式双氧化方法。该方法采用催化量的水合三氯化钌作为催化剂,30%的双氧水作为氧化剂,具有独特的化学、立体和区域三重选择性。
本文第一部分报道了此新型芳基取代烯烃的顺式双氧化方法的探索及其优化过程。该方法以0.02当量水合三氯化钌为催化剂、以2当量30%的双氧水,在室温条件下,15分钟内成功地将反式菧氧化得到2-羟基-1,2-二苯基乙酸酯。
本文第二部分考察了新型催化氧化体系对于含碳碳双键的多种类型的化合物(包括脂肪链烯烃、芳基取代烯烃、吲哚衍生物等)的适用性,大量实验表明,此催化氧化体系,可广泛用于芳基取代烯烃的顺式双氧化反应,对吲哚类衍生物不能实现顺式双氧化,而是通过双氧水和乙酸生成的过氧乙酸对它们进行缓慢的环氧化反应,并最终得到反式双氧化产物,对于脂肪链烯烃没有氧化作用。根据以上实验结果,我们推断此氧化体系可以实现在脂肪链碳碳双键存在的条件下选择性氧化芳基取代双键。
本文第三部分考察了新型催化氧化体系对同时含有脂肪链双键和芳基取代双键的二烯烃类化合物和芳基取代的共轭二烯烃(或三烯烃)的选择性双氧化能力。实验表明,此催化氧化体系可以在不破坏脂肪链碳碳双键的条件下,将芳基取代双键成功的进行选择性氧化,并且,此反应体系可以实现芳基取代双键的化学、立体和区域三重选择性氧化。芳基取代的共轭多烯烃,则得到端位双键被氧化的产物。
本论文第四部分根据此催化氧化体系反应速度快的特点,选取了几种芳基取代烯烃测定了它们的TON和TOF数据。同时,根据对实验现象和结果的分析提出了可能的反应机理,并且通过实验验证了机理的合理性。
总之,本文报道的芳基取代烯烃的选择性顺式双氧化方法,操作简单、反应条件温和、反应速度快、催化剂用量小、氧化剂价廉易得并且绿色环保,为有机化学和药物化学的发展提供了有力的支持。此方法首次实现了芳基取代烯烃的化学、立体、区域三重选择性氧化,可以为某些化工和医药原料或中间体的合成提供新的途径。
A novel, economical and environmentally friendly synthesis of aryl glycol monoesters from aryl olefins using hydrogen peroxide as the final oxidant catalyzed by ruthenium chloride has been reported in this dissertation.
The heuristic and optimizing process of this new aryl olefin selective oxidation system has been reported in the first part of this dissertation. We performed a set of preliminary experiments on stilbene as a model substrate using 30% hydrogen peroxide in the presence of various catalysts and solvents at room temperature. Finally, an efficient dioxygenation system of aryl olefins with 0.02 eq ruthenium chloride as catalyst and using 2 eq 30% hydrogen peroxide as oxidant was established.
The applicability of this new catalytic oxidation system has been examined in the second part of this dissertation. Various aryl olefins were converted into the corresponding aryl glycol monoesters with in 15-40 min at room temperature, while this catalytic oxidation system has no effect on alkyl olefins. Indole derivatives were dioxygenated slowly under the oxidation of peracetic acid which was formed from acetic acid and hydrogen peroxide, and gave trans dioxygenation products.
The chemoselective dioxygenation of aryl carbon-carbon double bonds of this new catalytic oxidation system has been investigated in the third part of this dissertation. Experiments of intramolecular competition showed that the procedure could be successfully used in the selective dioxygenation of aryl carbon-carbon double bonds with no influence on alkyl carbon-carbon double bonds.
Another outstanding characteristic has been examined in the forth part of this dissertation. We select several substrates and test the TON and TOF of their oxidation under this system. Moreover, a plausible concerted [5+2] cycloaddition mechanism for the selective dioxygenation of aryl olefins is proposed.
In conclusion, the first chemo-, regio-, and stereoselectivity dioxygenation of aryl olefins reported herein are operationally simple, and with superior economical and environmentally friendly characteristics. It represents new routs for the synthesis of some chemical and pharmaceutical products.
本文第一部分报道了此新型芳基取代烯烃的顺式双氧化方法的探索及其优化过程。该方法以0.02当量水合三氯化钌为催化剂、以2当量30%的双氧水,在室温条件下,15分钟内成功地将反式菧氧化得到2-羟基-1,2-二苯基乙酸酯。
本文第二部分考察了新型催化氧化体系对于含碳碳双键的多种类型的化合物(包括脂肪链烯烃、芳基取代烯烃、吲哚衍生物等)的适用性,大量实验表明,此催化氧化体系,可广泛用于芳基取代烯烃的顺式双氧化反应,对吲哚类衍生物不能实现顺式双氧化,而是通过双氧水和乙酸生成的过氧乙酸对它们进行缓慢的环氧化反应,并最终得到反式双氧化产物,对于脂肪链烯烃没有氧化作用。根据以上实验结果,我们推断此氧化体系可以实现在脂肪链碳碳双键存在的条件下选择性氧化芳基取代双键。
本文第三部分考察了新型催化氧化体系对同时含有脂肪链双键和芳基取代双键的二烯烃类化合物和芳基取代的共轭二烯烃(或三烯烃)的选择性双氧化能力。实验表明,此催化氧化体系可以在不破坏脂肪链碳碳双键的条件下,将芳基取代双键成功的进行选择性氧化,并且,此反应体系可以实现芳基取代双键的化学、立体和区域三重选择性氧化。芳基取代的共轭多烯烃,则得到端位双键被氧化的产物。
本论文第四部分根据此催化氧化体系反应速度快的特点,选取了几种芳基取代烯烃测定了它们的TON和TOF数据。同时,根据对实验现象和结果的分析提出了可能的反应机理,并且通过实验验证了机理的合理性。
总之,本文报道的芳基取代烯烃的选择性顺式双氧化方法,操作简单、反应条件温和、反应速度快、催化剂用量小、氧化剂价廉易得并且绿色环保,为有机化学和药物化学的发展提供了有力的支持。此方法首次实现了芳基取代烯烃的化学、立体、区域三重选择性氧化,可以为某些化工和医药原料或中间体的合成提供新的途径。
A novel, economical and environmentally friendly synthesis of aryl glycol monoesters from aryl olefins using hydrogen peroxide as the final oxidant catalyzed by ruthenium chloride has been reported in this dissertation.
The heuristic and optimizing process of this new aryl olefin selective oxidation system has been reported in the first part of this dissertation. We performed a set of preliminary experiments on stilbene as a model substrate using 30% hydrogen peroxide in the presence of various catalysts and solvents at room temperature. Finally, an efficient dioxygenation system of aryl olefins with 0.02 eq ruthenium chloride as catalyst and using 2 eq 30% hydrogen peroxide as oxidant was established.
The applicability of this new catalytic oxidation system has been examined in the second part of this dissertation. Various aryl olefins were converted into the corresponding aryl glycol monoesters with in 15-40 min at room temperature, while this catalytic oxidation system has no effect on alkyl olefins. Indole derivatives were dioxygenated slowly under the oxidation of peracetic acid which was formed from acetic acid and hydrogen peroxide, and gave trans dioxygenation products.
The chemoselective dioxygenation of aryl carbon-carbon double bonds of this new catalytic oxidation system has been investigated in the third part of this dissertation. Experiments of intramolecular competition showed that the procedure could be successfully used in the selective dioxygenation of aryl carbon-carbon double bonds with no influence on alkyl carbon-carbon double bonds.
Another outstanding characteristic has been examined in the forth part of this dissertation. We select several substrates and test the TON and TOF of their oxidation under this system. Moreover, a plausible concerted [5+2] cycloaddition mechanism for the selective dioxygenation of aryl olefins is proposed.
In conclusion, the first chemo-, regio-, and stereoselectivity dioxygenation of aryl olefins reported herein are operationally simple, and with superior economical and environmentally friendly characteristics. It represents new routs for the synthesis of some chemical and pharmaceutical products.
引文
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