铑催化的吡啶直接官能团化及芳烃乙烯基化
摘要
近七年,铑催化的C-H活化发展十分迅猛,很多官能团导向的C-H活化反应被陆续报道出来,特别是铑在C-H活化后对烯烃和炔烃的插入反应方面,具有强大的催化效率。吡啶是一个常见的结构单元,在医药、农药以及光学材料科学方面有着广泛的应用,快速地构建、衍生吡啶环在有机合成中显得尤为重要。吡啶的C2选择性官能团化已经有很多报道,但是,吡啶C3选择性官能团化还比较少。因此,我们试图用铑来发展毗啶C3选择性官能团化以及开发铑催化的新反应。本论文主要内容如下：
1、特戊酰胺导向的铑催化吡啶C3氧化烯基化
通过吡啶C2位的导向基—特戊酰胺基的作用,选择性烯基化在毗啶C3位。反应经过了铑催化的C-H活化,其中,醋酸铜可能既作氧化剂又作路易斯酸。另外,导向基部分同时也是一个很好的官能团,可以发生各种转化,我们成功将其应用到萘啶酮衍生物的高效合成中。
2、铑催化烟酰胺C3氧化烯基化
以毗啶C2位的三级酰胺为导向基,使得C-H活化选择性发生在C3位。反应的普适性很好,产率优秀。当采用二级酰胺时,则得到分子内进一步环合的产物,产物双键的构型由NOE确认。
3、官能团导向的铑催化碳氢活化：末端芳基乙烯的合成
通过导向的铑催化C-H活化,然后与乙烯基三乙氧基硅烷发生偶联反应。导向基可以是吡咯烷酮、特戊酰基、乙酰基、苯甲酰胺,甚至弱导向的芳基酮都可以导向邻位C-H活化烯基化反应。尽管存在一定的物料不守恒,反应的产率中等到良好。
In the past seven years, Rh-Catalyzed C-H activation has got stupendous progress and shows powerful catalysis efficiency since more and more publications about chelation assistance have been reported, especially on coupling with alkenes and alkynes. The pyridine ring is a common motif found in nature and have extensive application in pharmaceuticals, agrochemicals, as well as material science. Consequently, tremendous efforts have been made to construct these scaffolds. There are quite a few reports on C2-H functionalization of pyridines, however, there are still few reports on C3-H. Hence, we try to apply Rh to C3-H functionalization of pyridines and explore much more reaction types on Rh Catalysis. The main content of this dissertation is summarize as follows:
1. Rhodium(Ⅲ)-Catalyzed Oxidative Olefination of Pyridines and Quinolines
we have achieved the effective oxidative olefination of both pyridine pivalamides and quinoline pivalamides at the ortho-position of the directing group, which involves a rhodium(Ⅲ)-catalyzed C-H activation pathway using Cu(OAc)2as a convenient oxidant as well as Lewis acid. The pivalamide not only serves as a directing group, but also could be considered as a protecting group. This protocol was operationally simple and could be successfully applied to an expeditious, multigram-scale synthesis of naphthyridinone with low catalyst loading.
2. Rh(Ⅲ)-Catalyzed Oxidative Olefination of Picolinamides:Convenient Synthesis of3-Alkeny lpicolinamides
We have developed an efficient Rh(Ⅲ)-catalyzed oxidative olefination of picolinamides with carboxamides as directing groups. The reaction protocol provides an expedient route to the functionalization of pyridine derivatives with several advantages, including low catalyst loading (0.5mol%in most cases), high yield and good functional group tolerance. When secondary piconilamides were coupled to ethyl acrylate, the olefination-cyclization products were obtained in good yields. The E configuration of the exocyclic double bond was confirmed by NOESY.
3. Rh(III)-Catalyzed C-H Activation of Arenes via chelation assistance:Access to Terminal Alkenes
We have found that arenes could couple with vinytriethoxysilane to form terminal alkenes, which undergoes Rh(III)-catalyzed C-H activation of arenes via chelation assistance. The directing groups can be pyrrolidones, pivalamides, benzamides as well as aryl ketones, which are weakly directing groups. The reaction proceeded with moderate yields due to the unbalanced materials.
1、特戊酰胺导向的铑催化吡啶C3氧化烯基化
通过吡啶C2位的导向基—特戊酰胺基的作用,选择性烯基化在毗啶C3位。反应经过了铑催化的C-H活化,其中,醋酸铜可能既作氧化剂又作路易斯酸。另外,导向基部分同时也是一个很好的官能团,可以发生各种转化,我们成功将其应用到萘啶酮衍生物的高效合成中。
2、铑催化烟酰胺C3氧化烯基化
以毗啶C2位的三级酰胺为导向基,使得C-H活化选择性发生在C3位。反应的普适性很好,产率优秀。当采用二级酰胺时,则得到分子内进一步环合的产物,产物双键的构型由NOE确认。
3、官能团导向的铑催化碳氢活化：末端芳基乙烯的合成
通过导向的铑催化C-H活化,然后与乙烯基三乙氧基硅烷发生偶联反应。导向基可以是吡咯烷酮、特戊酰基、乙酰基、苯甲酰胺,甚至弱导向的芳基酮都可以导向邻位C-H活化烯基化反应。尽管存在一定的物料不守恒,反应的产率中等到良好。
In the past seven years, Rh-Catalyzed C-H activation has got stupendous progress and shows powerful catalysis efficiency since more and more publications about chelation assistance have been reported, especially on coupling with alkenes and alkynes. The pyridine ring is a common motif found in nature and have extensive application in pharmaceuticals, agrochemicals, as well as material science. Consequently, tremendous efforts have been made to construct these scaffolds. There are quite a few reports on C2-H functionalization of pyridines, however, there are still few reports on C3-H. Hence, we try to apply Rh to C3-H functionalization of pyridines and explore much more reaction types on Rh Catalysis. The main content of this dissertation is summarize as follows:
1. Rhodium(Ⅲ)-Catalyzed Oxidative Olefination of Pyridines and Quinolines
we have achieved the effective oxidative olefination of both pyridine pivalamides and quinoline pivalamides at the ortho-position of the directing group, which involves a rhodium(Ⅲ)-catalyzed C-H activation pathway using Cu(OAc)2as a convenient oxidant as well as Lewis acid. The pivalamide not only serves as a directing group, but also could be considered as a protecting group. This protocol was operationally simple and could be successfully applied to an expeditious, multigram-scale synthesis of naphthyridinone with low catalyst loading.
2. Rh(Ⅲ)-Catalyzed Oxidative Olefination of Picolinamides:Convenient Synthesis of3-Alkeny lpicolinamides
We have developed an efficient Rh(Ⅲ)-catalyzed oxidative olefination of picolinamides with carboxamides as directing groups. The reaction protocol provides an expedient route to the functionalization of pyridine derivatives with several advantages, including low catalyst loading (0.5mol%in most cases), high yield and good functional group tolerance. When secondary piconilamides were coupled to ethyl acrylate, the olefination-cyclization products were obtained in good yields. The E configuration of the exocyclic double bond was confirmed by NOESY.
3. Rh(III)-Catalyzed C-H Activation of Arenes via chelation assistance:Access to Terminal Alkenes
We have found that arenes could couple with vinytriethoxysilane to form terminal alkenes, which undergoes Rh(III)-catalyzed C-H activation of arenes via chelation assistance. The directing groups can be pyrrolidones, pivalamides, benzamides as well as aryl ketones, which are weakly directing groups. The reaction proceeded with moderate yields due to the unbalanced materials.
引文
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