钯催化的羰基化偶联反应研究
摘要
本论文由两部分内容组成：
第一篇是关于Pd催化反应的研究进展综述。该篇共分两章对文献进行了综述。第一章：第一节中主要介绍了过渡金属Pd催化的偶联反应在C-C键的构建中的应用，对其中涉及到的典型偶联反应如：Negishi偶联、Sonogashira偶联、Still偶联、Kumada偶联、Hiyama偶联、Heck偶联、Suzuki偶联等七种偶联反应的提出、反应的基本机理、有机合成反应中C-C键构建的应用、前人所作同类反应的研究报道及其所解决的问题作了文献综述。第二节在对Pd催化下偶联反应中C-C键构建文献综述的基础上，对Pd催化下的C-N、C-O、C-P、C-S等碳-杂原子键的构建从反应方法的提出、反应机理的阐述、反应中各方面条件的选择控制及前人所作的同类研究报道进行了文献综述。在第二章中，对Pd催化的羰基化反应进行了综述。以上两方面的文献综述对于了解Pd催化下偶联反应的研究进展有一定的文献帮助作用，便于在文献参考的基础上，对实际反应过程中遇到的理论和实验问题加以解决，有一定的指导作用。
第二篇是论文的实验研究部分，在这部分内容中主要进行了以下二个方面的研究：一、通过Pd催化的Sonogashira羰基化偶联反应，合成了一系列的二茂铁乙炔基芳基酮化合物。在1 atm CO下，反应以二茂铁乙炔和芳基碘化物为原料，Pd(PPh_3)_4／CuI作催化剂，K_2CO_3作碱，甲苯为溶剂，以较高的产率获得目标产物。该反应原料易于制备，操作简便，反应时间短(90 min)。特别是当芳基上取代基是供电子基团时，产物是羰基化偶联产物，直接偶联的非羰基化产物在实验中并没有检测出。二、通过Pd催化的Sonogashira羰基化环化反应，首次合成了7个2-二茂铁基取代的苯并-γ-吡喃酮。在1 atm CO下，反应以二茂铁乙炔和邻碘苯酚(或4-取代的邻碘苯酚)为原料，Pd(PPh_3)_4／CuI作催化剂，K_2CO_3作碱，甲苯为溶剂，在较短的反应时间(90 min)里以较高的产率获得目标产物。此反应可用于合成二茂铁取代的黄酮类化合物及其衍生物。
The thesis consists of two parts:
The first part is to summarize the development of coupling reaction catalyzed by palladium. The first section of this part summarize the wide application of coupling reaction catalyzed by Palladium in the confirmation of C-C and carbon-heteroatom bond. The coupling reaction involving Negishi Coupling reaction, Sonogashira Coupling reaction, Still Coupling reaction, Kumada Coupling reaction, Hiyama Coupling reaction, Heck Coupling reaction and Suzuki Coupling. The second section of this part is the review on carbonylative coupling reaction catalyzed by Palladium.
The second part is our study on the synthesis of ferrocenylethynyl aryl ketones and2-Ferrocenyl-4H-chromen-4-ones. The first section of this part is the convenient synthesis of ferrocenylethynyl aryl ketones via Palladium-Catalyzed Sonogashira carbonylation coupling reaction. The reaction was performed in short time and in good yield using ethynylferrocene and ArI as the starting materials Pd(PPh_3)_4/CuI as catalyst, K_2CO_3 as base, toluene as solvent under CO (1 atm). The second section is the synthesis of seven 2-Ferrocenyl-4H-chromen-4-ones via carbonylation coupling-annulation catalyzed by Palladium for the first time. Ethynylferrocene and 2-iodophenol are used as the starting materials, Pd(PPh_3)_4/CuI as catalyst, K_2CO_3 as base. The reaction is performed under CO (1 atm) to obtain the objective products in short time and good yield. This synthetic procedure can be applied in the synthesis of flavonoids and chromones derivatives substituted by ferrocene.
第一篇是关于Pd催化反应的研究进展综述。该篇共分两章对文献进行了综述。第一章：第一节中主要介绍了过渡金属Pd催化的偶联反应在C-C键的构建中的应用，对其中涉及到的典型偶联反应如：Negishi偶联、Sonogashira偶联、Still偶联、Kumada偶联、Hiyama偶联、Heck偶联、Suzuki偶联等七种偶联反应的提出、反应的基本机理、有机合成反应中C-C键构建的应用、前人所作同类反应的研究报道及其所解决的问题作了文献综述。第二节在对Pd催化下偶联反应中C-C键构建文献综述的基础上，对Pd催化下的C-N、C-O、C-P、C-S等碳-杂原子键的构建从反应方法的提出、反应机理的阐述、反应中各方面条件的选择控制及前人所作的同类研究报道进行了文献综述。在第二章中，对Pd催化的羰基化反应进行了综述。以上两方面的文献综述对于了解Pd催化下偶联反应的研究进展有一定的文献帮助作用，便于在文献参考的基础上，对实际反应过程中遇到的理论和实验问题加以解决，有一定的指导作用。
第二篇是论文的实验研究部分，在这部分内容中主要进行了以下二个方面的研究：一、通过Pd催化的Sonogashira羰基化偶联反应，合成了一系列的二茂铁乙炔基芳基酮化合物。在1 atm CO下，反应以二茂铁乙炔和芳基碘化物为原料，Pd(PPh_3)_4／CuI作催化剂，K_2CO_3作碱，甲苯为溶剂，以较高的产率获得目标产物。该反应原料易于制备，操作简便，反应时间短(90 min)。特别是当芳基上取代基是供电子基团时，产物是羰基化偶联产物，直接偶联的非羰基化产物在实验中并没有检测出。二、通过Pd催化的Sonogashira羰基化环化反应，首次合成了7个2-二茂铁基取代的苯并-γ-吡喃酮。在1 atm CO下，反应以二茂铁乙炔和邻碘苯酚(或4-取代的邻碘苯酚)为原料，Pd(PPh_3)_4／CuI作催化剂，K_2CO_3作碱，甲苯为溶剂，在较短的反应时间(90 min)里以较高的产率获得目标产物。此反应可用于合成二茂铁取代的黄酮类化合物及其衍生物。
The thesis consists of two parts:
The first part is to summarize the development of coupling reaction catalyzed by palladium. The first section of this part summarize the wide application of coupling reaction catalyzed by Palladium in the confirmation of C-C and carbon-heteroatom bond. The coupling reaction involving Negishi Coupling reaction, Sonogashira Coupling reaction, Still Coupling reaction, Kumada Coupling reaction, Hiyama Coupling reaction, Heck Coupling reaction and Suzuki Coupling. The second section of this part is the review on carbonylative coupling reaction catalyzed by Palladium.
The second part is our study on the synthesis of ferrocenylethynyl aryl ketones and2-Ferrocenyl-4H-chromen-4-ones. The first section of this part is the convenient synthesis of ferrocenylethynyl aryl ketones via Palladium-Catalyzed Sonogashira carbonylation coupling reaction. The reaction was performed in short time and in good yield using ethynylferrocene and ArI as the starting materials Pd(PPh_3)_4/CuI as catalyst, K_2CO_3 as base, toluene as solvent under CO (1 atm). The second section is the synthesis of seven 2-Ferrocenyl-4H-chromen-4-ones via carbonylation coupling-annulation catalyzed by Palladium for the first time. Ethynylferrocene and 2-iodophenol are used as the starting materials, Pd(PPh_3)_4/CuI as catalyst, K_2CO_3 as base. The reaction is performed under CO (1 atm) to obtain the objective products in short time and good yield. This synthetic procedure can be applied in the synthesis of flavonoids and chromones derivatives substituted by ferrocene.
引文
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