过渡金属催化碳—碳键偶联反应研究
摘要
本文由两部分组成,其中第一部分(前三章)为过渡金属催化有机合成方法学方面的基础理论研究;第二部分(后两章)为实用有机合成方法学研究。
1.过渡金属催化有机合成方法学研究(前三章)。
这部分通过对钯、铑、铁等过渡金属催化有机合成反应的深入研究,发展了三类新颖反应。一,发展了钯催化的炔丙基碳酸酯与有机锌试剂的串联氧化环化反应,并制备了一类含有烯丙基碳酸酯片断的新颖茚类化合物;二,发展了铑催化的碳氢活化酯基化反应,选择性的将惰性苯环碳氢键官能团化为酯基;三,开发了铁催化的碳氢活化氧化偶联反应,制备了一系列取代的吲哚类化合物。
2.实用有机合成方法学研究。
针对有机合成和工业生产中的需求,我们完成了两类化合物的实用合成方法学研究,这两类方法最大的特点就是经济、方便并且操作简单。第一类,我们发展了铑碳催化还原酰化酮肟制备烯酰胺类化合物的方法学。第二类,我们用简单易得的1,2-二溴化合物跟亚磺酸钠盐反应,开发了高效、简便的制备取代烯基砜化合物的合成方法。
The thesis is composed of two parts.The first part(Chapters 1-3) involves the fundamental studies of transition metal catalyzed organic transformation.The second part presents the practical synthesis of important building blocks in organic chemistry.
PartⅠ.Transition metal catalyzed organic reactions(Chapters 1-3).
We have developed three new synthetic reactions through intensively investigation of the transition metal catalyzed organic reactions.Chapter 1 describes a straightforward,very useful approach to a new and important class of indene derivatives by Pd-catalyzed tandem cyclization of propargylic carbonates with in situ generated organozinc compounds.Chapter 2 presents a mild and general procedure for the Rh-catalyzed oxidative carbonylation of aryl C-H bonds with carbon monoxide and alcohols.Chapter 3 exhibits an efficient Fe-catalyzed intramolecular oxidative coupling of aryl C-H and vinyl C-H bonds for preparation of valuable substituted indole products.
PartⅡ.Practical synthesis of important building blocks(Chapters 4-5).
In this part,we present two mild and practical procedures for preparation of enamides and vinyl sulfones which both the important building blocks in organic chemistry.Chapter 4 exhibits a practical method for the Rh/C-catalyzed direct hydroacylation of ketoximes for preparation of enamides.And in chapter 5,we describe a practical process for the synthesis of vinyl sulfones from dibromides and commercially available sulfinic acid sodium salts in DMF.
1.过渡金属催化有机合成方法学研究(前三章)。
这部分通过对钯、铑、铁等过渡金属催化有机合成反应的深入研究,发展了三类新颖反应。一,发展了钯催化的炔丙基碳酸酯与有机锌试剂的串联氧化环化反应,并制备了一类含有烯丙基碳酸酯片断的新颖茚类化合物;二,发展了铑催化的碳氢活化酯基化反应,选择性的将惰性苯环碳氢键官能团化为酯基;三,开发了铁催化的碳氢活化氧化偶联反应,制备了一系列取代的吲哚类化合物。
2.实用有机合成方法学研究。
针对有机合成和工业生产中的需求,我们完成了两类化合物的实用合成方法学研究,这两类方法最大的特点就是经济、方便并且操作简单。第一类,我们发展了铑碳催化还原酰化酮肟制备烯酰胺类化合物的方法学。第二类,我们用简单易得的1,2-二溴化合物跟亚磺酸钠盐反应,开发了高效、简便的制备取代烯基砜化合物的合成方法。
The thesis is composed of two parts.The first part(Chapters 1-3) involves the fundamental studies of transition metal catalyzed organic transformation.The second part presents the practical synthesis of important building blocks in organic chemistry.
PartⅠ.Transition metal catalyzed organic reactions(Chapters 1-3).
We have developed three new synthetic reactions through intensively investigation of the transition metal catalyzed organic reactions.Chapter 1 describes a straightforward,very useful approach to a new and important class of indene derivatives by Pd-catalyzed tandem cyclization of propargylic carbonates with in situ generated organozinc compounds.Chapter 2 presents a mild and general procedure for the Rh-catalyzed oxidative carbonylation of aryl C-H bonds with carbon monoxide and alcohols.Chapter 3 exhibits an efficient Fe-catalyzed intramolecular oxidative coupling of aryl C-H and vinyl C-H bonds for preparation of valuable substituted indole products.
PartⅡ.Practical synthesis of important building blocks(Chapters 4-5).
In this part,we present two mild and practical procedures for preparation of enamides and vinyl sulfones which both the important building blocks in organic chemistry.Chapter 4 exhibits a practical method for the Rh/C-catalyzed direct hydroacylation of ketoximes for preparation of enamides.And in chapter 5,we describe a practical process for the synthesis of vinyl sulfones from dibromides and commercially available sulfinic acid sodium salts in DMF.
引文
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