基于新导向基拓展的Pd催化C-H键官能团化
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摘要
Pd催化的导向C-H官能团化由于可以给传统有机化学的逆合成分析提供新的思路而成为近年来方法学的热点内容。本论文首先综述了Pd催化C-H键官能化的发展历史和现状,列举了非导向和导向C-H活化的反应实例,比较了不同导向基团的反应特性,从而得出结论:将导向C-H官能团化真正应用于有机合成的关键在于必须使可以用于导向的基团更加丰富多元化。
我们选择了酚酯入手,针对Pd与氧导向基络合弱的问题,我们发现在三氟甲磺酸(HOTf)的促进下,酚酯成功地与Pd进行络合并且导向在邻位发生了C-H键的活化。我们成功分离和表征了关键的环钯中间体,这是首例酚酯导向的环钯化合物。接下来,在Pd(II)-HOTf的催化下,酚的不同酯保护基例如乙酸酯、特戊酸酯、苯甲酸酯以及氨基甲酸酯都可以二芳基碘盐发生邻位的芳基化反应,其中以特戊酸酯效果最好。新方法提供了一种合成2-芳基酚衍生物的途径,并且被证明在一些生理活性分子的合成以及手性联萘酚配体的衍生方面具有价值。
沿着这样的思路,我们选择与酚酯同样弱配位,并且C-H键缺电子的芳香酮为底物;而另一边我们选择偶联反应研究尚不多的酰胺。我们发现HOTf同样促进了环钯的形成,并且在强氧化剂例如过硫酸钠或者F+试剂的作用下,成功实现与酰胺的C-N偶联。更为重要的是,此前人们普遍认为C-H活化/C-N偶联的机理是一个N卡宾插入C-Pd键的过程,而我们的工作揭示出一种新的途径,即酰胺直接与环钯中间体的Pd原子配位,在氧化剂的作用下形成Pd(IV)中间体,最后发生N-的还原消除。反应产物邻氨基酮通过我们的衍生用来合成了一系列吲哚化合物,以及一个降血糖药物Prandin的关键中间体。
此外,我们发现邻苯基苯酚导向的C-H活化只能实现分子间的交叉偶联,而不能够进行分子内的还原消除。针对这一现象,我们通过同位素实验研究发现酚导向的C-H活化实际上是很容易发生的,但是还原消除的困难制约了分子内的环合。通过很多尝试,我们发现在羧酸阴离子和卡宾配体IPr的促进下,以空气为氧化剂可以得到分子内环合的二苯并呋喃产物,并且获得了环钯中间体的晶体结构。在这个晶体结构的启示下,我们调整羧酸阴离子,最终确定2,4,6-三甲基苯甲酸钠(MesCOONa)效果最佳,实现了较高产率的分子内C-O交叉偶联。该方法可以合成一系列取代的二苯并呋喃衍生物。
Pd-catalyzed direct C-H functionalization has been emerged as a novel strategy in the traditional retrosynthetic analysis of total synthesis. It has been a central problem of the methodology during the past decades. This thesis mainly focuses on the Reactions of new directing groups in Pd-catalyzed C-H functionalization. The main contents include:
The first chapter simply reviews the Pd -catalyzed C-H bond functionaliztion history and the current status of the development. By comparing the examples of C-H bond activation reactions of Pd catalysts with the other metal catalysts, we finally concluded the unique characters and the frontier of the Pd chemistry.
In chapter 2, we think the key point to apply direct C-H functionaliztion in organic synthesis is to diversify the directing groups. In order to solve the problem of poor coordination ability of Pd with O-directing group, we choose phenol esters as the substrate. With the promotion of catalytic amount of strong acid (HOTf), we first reported the phenol ester directed C-H/Aryl-Aryl coupling with diaryliodonium triflates reaction and characterized the key intermediates. This new protocol provides a new method to synthesize 2-arylphenols, inhibitors of EGF-stimulated cellular proliferation and 3,3’-bis-arylated-BINOLs.
In chapter 3, we further choose aromatic ketones as substrate which shows similar low coordination abilities as phenol esters with much more electron-deficiency. We choose amides as the coupling partner considering that amides are lack of attentions in cross coupling reactions. We discovered HOTf also promoted the cyclopalladation, and successfully realized the C-N coupling of 4-chlorophenyl sulfonamide. Meanwhile, we indicated that the new reaction does not seem to proceed through a nitrene intermediate, but much more like through N- reductive elimination. The mechanism is a new aspect in Pd chemistry.
In addition, we found that the direct C-H activation on o-arylphenol could only be achieved via the cross coupling strategy intermolecularly, while the intramolecular reductive elimination in activating of C-H bond on o-arylphenol has rarely been reported. In response to this phenomenon, we found phenol directed C-H activation was very easy to take place, but the difficulty of reductive elimination retarded the intramolecular cyclization. By tuning the Carboxylic acid anion and the ligand, we successfully realized the high yield of intramolecular C-O cross coupling. This method can provide a series of functionalized dibenzofuran derivatives.
我们选择了酚酯入手,针对Pd与氧导向基络合弱的问题,我们发现在三氟甲磺酸(HOTf)的促进下,酚酯成功地与Pd进行络合并且导向在邻位发生了C-H键的活化。我们成功分离和表征了关键的环钯中间体,这是首例酚酯导向的环钯化合物。接下来,在Pd(II)-HOTf的催化下,酚的不同酯保护基例如乙酸酯、特戊酸酯、苯甲酸酯以及氨基甲酸酯都可以二芳基碘盐发生邻位的芳基化反应,其中以特戊酸酯效果最好。新方法提供了一种合成2-芳基酚衍生物的途径,并且被证明在一些生理活性分子的合成以及手性联萘酚配体的衍生方面具有价值。
沿着这样的思路,我们选择与酚酯同样弱配位,并且C-H键缺电子的芳香酮为底物;而另一边我们选择偶联反应研究尚不多的酰胺。我们发现HOTf同样促进了环钯的形成,并且在强氧化剂例如过硫酸钠或者F+试剂的作用下,成功实现与酰胺的C-N偶联。更为重要的是,此前人们普遍认为C-H活化/C-N偶联的机理是一个N卡宾插入C-Pd键的过程,而我们的工作揭示出一种新的途径,即酰胺直接与环钯中间体的Pd原子配位,在氧化剂的作用下形成Pd(IV)中间体,最后发生N-的还原消除。反应产物邻氨基酮通过我们的衍生用来合成了一系列吲哚化合物,以及一个降血糖药物Prandin的关键中间体。
此外,我们发现邻苯基苯酚导向的C-H活化只能实现分子间的交叉偶联,而不能够进行分子内的还原消除。针对这一现象,我们通过同位素实验研究发现酚导向的C-H活化实际上是很容易发生的,但是还原消除的困难制约了分子内的环合。通过很多尝试,我们发现在羧酸阴离子和卡宾配体IPr的促进下,以空气为氧化剂可以得到分子内环合的二苯并呋喃产物,并且获得了环钯中间体的晶体结构。在这个晶体结构的启示下,我们调整羧酸阴离子,最终确定2,4,6-三甲基苯甲酸钠(MesCOONa)效果最佳,实现了较高产率的分子内C-O交叉偶联。该方法可以合成一系列取代的二苯并呋喃衍生物。
Pd-catalyzed direct C-H functionalization has been emerged as a novel strategy in the traditional retrosynthetic analysis of total synthesis. It has been a central problem of the methodology during the past decades. This thesis mainly focuses on the Reactions of new directing groups in Pd-catalyzed C-H functionalization. The main contents include:
The first chapter simply reviews the Pd -catalyzed C-H bond functionaliztion history and the current status of the development. By comparing the examples of C-H bond activation reactions of Pd catalysts with the other metal catalysts, we finally concluded the unique characters and the frontier of the Pd chemistry.
In chapter 2, we think the key point to apply direct C-H functionaliztion in organic synthesis is to diversify the directing groups. In order to solve the problem of poor coordination ability of Pd with O-directing group, we choose phenol esters as the substrate. With the promotion of catalytic amount of strong acid (HOTf), we first reported the phenol ester directed C-H/Aryl-Aryl coupling with diaryliodonium triflates reaction and characterized the key intermediates. This new protocol provides a new method to synthesize 2-arylphenols, inhibitors of EGF-stimulated cellular proliferation and 3,3’-bis-arylated-BINOLs.
In chapter 3, we further choose aromatic ketones as substrate which shows similar low coordination abilities as phenol esters with much more electron-deficiency. We choose amides as the coupling partner considering that amides are lack of attentions in cross coupling reactions. We discovered HOTf also promoted the cyclopalladation, and successfully realized the C-N coupling of 4-chlorophenyl sulfonamide. Meanwhile, we indicated that the new reaction does not seem to proceed through a nitrene intermediate, but much more like through N- reductive elimination. The mechanism is a new aspect in Pd chemistry.
In addition, we found that the direct C-H activation on o-arylphenol could only be achieved via the cross coupling strategy intermolecularly, while the intramolecular reductive elimination in activating of C-H bond on o-arylphenol has rarely been reported. In response to this phenomenon, we found phenol directed C-H activation was very easy to take place, but the difficulty of reductive elimination retarded the intramolecular cyclization. By tuning the Carboxylic acid anion and the ligand, we successfully realized the high yield of intramolecular C-O cross coupling. This method can provide a series of functionalized dibenzofuran derivatives.
引文
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16.最近,Gaunt课题组发展了一种三氟甲磺酸铜催化的雌酮邻位直接芳基化反应,芳基化试剂也是使用I(III)盐,但是对于我们要引入的带甲酯基的芳环效果较差:Ciana, C.-L.; Phipps, R. J.; Brandt, J. R.; Meyer, F.-M.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 458.
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16.最近,Gaunt课题组发展了一种三氟甲磺酸铜催化的雌酮邻位直接芳基化反应,芳基化试剂也是使用I(III)盐,但是对于我们要引入的带甲酯基的芳环效果较差:Ciana, C.-L.; Phipps, R. J.; Brandt, J. R.; Meyer, F.-M.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 458.