金属催化重氮化合物参与的多取代呋喃合成研究
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摘要
本论文以过渡金属催化的重氮卡宾参与的多取代呋喃合成的新方法为主要研究对象，全文共分两个部分，内容概要如下：
第一章重氮化合物在有机合成中的应用研究进展
本章主要对过渡金属催化的重氮化学的研究历史进行了概述，重点介绍了近年来发表的最新研究成果，特别是源自α-重氮羰基化合物的金属卡宾转移反应。对于重氮卡宾参与的重要化学反应类型诸如X-H键(例如C-H，O-H键)的插入反应，环丙烷化反应，叶立德形成及后继反应等及其在有机合成中的应用分别作了详细的综述。
第二章：过渡金属催化的重氮卡宾参与的多取代呋喃合成研究
我们发展了一种高效的直接合成多取代呋喃衍生物的新方法。我们以Cu(Ⅰ)为催化剂，首次成功地实现了金属催化下α，β-炔酮与α-重氮乙酸酯的[4+1]环化反应。该[4+1]环化反应表现出了极好的区域选择性，该[4+1]环化反应原料廉价易得、条件温利，操作简单。此外，我们对这一新颖的环化反应的反应条件，底物适用范围进行了详细的考察，并在此基础上提出了一个可能的反应机理。所有新化合物结构不仅经过了核磁、元素分析和红外的测定，还得到了化合物3aa单晶的X-射线衍射的确认。
This thesis aims at the studies on the new method for synthesis of highly substituted furans with diazo compounds by transition-metal catalyzed, which mainly consists of the following parts:
Part I: The Recent Progress of Diazo Compounds in Organic Synthesis
The review summarizes the development of diazo chemistry and focuses mainly on the progress that has been made very recently, particularly in the field of catalytic metal carbene derived fromα-diazo carbonyl compounds transformations. The recent progress of them in organic synthetic reactions, such as the X-H bond (e.g., C-H, O-H) insertion reaction, cyclopropanation reaction, and ylide reaction of diazo carbene, was summarized in details.
Part II: Studies on the Synthesis of Highly Substituted Furans with Diazoacetates by transition-metal catalyzed
We have described the first examples of copper-catalyzed [4+1] cycloadditions ofα,β-acetylenic ketones withα-diazo esters. This new method furnished synthetically useful, highly substituted furan derivatives in a direct, one-flask process with good efficiency and regioselectivity. The protocol shows advantages in terms of its mild reaction condition simple operation, and easily available starting materials Furthermore, the reaction conditions and the scope of the process are examined, and a possible mechanism is proposed. All of the new compounds were characterized by not only NMR, and IR spectra, but also the single-crystal X-ray analysis in the case of the product 3aa.
第一章重氮化合物在有机合成中的应用研究进展
本章主要对过渡金属催化的重氮化学的研究历史进行了概述，重点介绍了近年来发表的最新研究成果，特别是源自α-重氮羰基化合物的金属卡宾转移反应。对于重氮卡宾参与的重要化学反应类型诸如X-H键(例如C-H，O-H键)的插入反应，环丙烷化反应，叶立德形成及后继反应等及其在有机合成中的应用分别作了详细的综述。
第二章：过渡金属催化的重氮卡宾参与的多取代呋喃合成研究
我们发展了一种高效的直接合成多取代呋喃衍生物的新方法。我们以Cu(Ⅰ)为催化剂，首次成功地实现了金属催化下α，β-炔酮与α-重氮乙酸酯的[4+1]环化反应。该[4+1]环化反应表现出了极好的区域选择性，该[4+1]环化反应原料廉价易得、条件温利，操作简单。此外，我们对这一新颖的环化反应的反应条件，底物适用范围进行了详细的考察，并在此基础上提出了一个可能的反应机理。所有新化合物结构不仅经过了核磁、元素分析和红外的测定，还得到了化合物3aa单晶的X-射线衍射的确认。
This thesis aims at the studies on the new method for synthesis of highly substituted furans with diazo compounds by transition-metal catalyzed, which mainly consists of the following parts:
Part I: The Recent Progress of Diazo Compounds in Organic Synthesis
The review summarizes the development of diazo chemistry and focuses mainly on the progress that has been made very recently, particularly in the field of catalytic metal carbene derived fromα-diazo carbonyl compounds transformations. The recent progress of them in organic synthetic reactions, such as the X-H bond (e.g., C-H, O-H) insertion reaction, cyclopropanation reaction, and ylide reaction of diazo carbene, was summarized in details.
Part II: Studies on the Synthesis of Highly Substituted Furans with Diazoacetates by transition-metal catalyzed
We have described the first examples of copper-catalyzed [4+1] cycloadditions ofα,β-acetylenic ketones withα-diazo esters. This new method furnished synthetically useful, highly substituted furan derivatives in a direct, one-flask process with good efficiency and regioselectivity. The protocol shows advantages in terms of its mild reaction condition simple operation, and easily available starting materials Furthermore, the reaction conditions and the scope of the process are examined, and a possible mechanism is proposed. All of the new compounds were characterized by not only NMR, and IR spectra, but also the single-crystal X-ray analysis in the case of the product 3aa.
引文
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