钯催化导向碳氢活化反应研究
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摘要
由于和氮、氧等杂原子的良好配位能力,过渡金属钯已成为导向C-H官能化最为有效的催化剂。迄今为止,对氮和氧导向的钯催化C-H活化已经得到广泛研究。虽然如此,寻找易于移除、易于转化的和新型导向基仍是日前研究导向C-H活化难点。本论文主要研究了易于转化的过渡金属钯催化2-亚砜吡啶及硫醚导向碳氢活化反应,本论文的主要内容包括：
1.2-亚砜吡啶导向Pd(OAc)2催化的C-H烯基化及芳基化反应研究
近年来,过渡金属催化的引导C-H活化得到了很好的发展,但其也存在一些问题,如引导基难以从产物中移除。因此这两年可移除的引导基也陆续被报导。我们采用2-亚砜吡啶为导向基,研究了在Pd(OAc)2催化下的芳基C-H烯基化及芳基化反应。研究表明,该体系中各种烯烃能够对取代的芳烃进行选择性C-2直接烯基化,产率从中等到良好。另外,也可以直接由简单的芳烃双C-H活化芳基化。特别是2-亚砜吡啶导向基可以通过选择性还原的方法既可以移除也可以转化成其它官能团,从而实现了我们预期的目标。
2.硫醚基团导向Pd(OAc)2催化的C-H键烯基化反应研究
硫醚是有机化合物中重要的结构单元,其在天然产物和药物中都广泛存在,同时在配位化学中也有广泛应用。我们研究了Pd(OAc)2催化的硫醚导向C-H键烯基化反应。产率从中等到良好,并且该反应具有区域选择性和立体选择性,一步生成(E)-异构体的2-位取代产物。并且在烯基化后,硫醚导向基可以在还原条件下移除或保留硫醚导向基团而还原双键：另外还可以选择性氧化成亚砜或砜,从而为进一步官能化提供了可能。
3. Pd(OAc)2催化丙烯酰胺类化合物Y位sp3C-H芳基化反应研究
虽然近年来sp3C-H官能化反应陆续被报道,但由于烷烃C-H键具有较高的活化能并且没有π电子的参与,因此非活性sp3C-H官能化仍是有机合成中的难点。我们知道,烯丙型的C-H键比孤立的sp3C-H键有更强的酸性,因此,我们对内烯酰胺类化合物γ位sp3C-H活化进行了研究。研究发现,在Pd(OAc)2催化下,膦配体作用时,芳基卤化物能够很好地对烯丙位C-H键进行芳基化,并且在芳基卤化物的位阻调配下,可以顺利地选择性进行双芳基化或单芳基化反应。产物中的双键发生了迁移,并且没有观察到α或β芳基化的副产物。同时,我们也对反应机理进行了比较深入的研究,为更深入了解sp3C-H官能化反应提供了依据。
For its ability of coordinating to nitrogen and oxygen, palladium have been becoming the most efficient catalyst for the directing C-H activation. Nowadays, O-containing and N-containing directing groups assisted C-H activation reaction catalyzed by palladium have been widely studied. In despite of this advance, to search the easily transformable, easily removable or newly tape of directing groups still the hot topic in directed C-H activation reaction currently.
This dissertation mainly focused on the studies of palladium catalyzed C-H bond activation assisted by the easily removable and transformable directing groups, which include:
1. Pd(OAc)2-catalyzed C-H alkenylatin and arylation of arenes assisted by removable2-pyridylsulfinyl Group
Nowadays, palladium-catalyzed chelation-directed C-H activation has been widely researched. However, in some cases the practicality might be restricted when the directing groups cannot easily be removed from the products. Therefore, significant effort has been directed toward the discovery of efficient and removable directing groups currently. We studied Pd(OAc)2-catalyzed C-H alkenylation and arylation of arenes assisted by removable2-pyridylsulfinyl group. It was found that a variety of alkenes selectively undergo the direct alkenylation in moderate to good yields. More importantly, this transformation could also be applied in arylation through dual C-H activation with simple arenes. Finally, as we expected, the2-pyridylsulfinyl group could be removed easily after the C-H bond functionalization under reductive conditions or afford diverse reduction products.
2. Pd(OAc)2-catalyzed C-H alkenylatin of arenes using thioether as directing groups
Thioether is an important structural motif in a wide range of molecules with numerous and important applications. It exists in drugs and natural product. It also has been widely used as coordination groups with various metals in many useful complexes. We studied Pd(OAc)2-catalyzed C-H alkenylation of arenes using thioether as directing groups. It was found that the alkenylation could undergo smoothly in moderate to good yields when using thioether as the directing group. It could obtain good regioselective and stereoselective. In most cases, the (E)-isomers were isolated as the major products; and the double alkenylated product can also be obtained with some special substrates. Finally, the alkenylated thioethers can be easily removed and transformed into a variety of useful groups.
3. Pd(OAc)2-catalyzed Regioselective y-Mono-and Diarylation of Acrylamide Derivatives with Aryl Halides
For the past several years, some examples about sp3C-H activation have been reported. But C(sp3)-H bond activation remains a challenging problem because of its high bond dissociation energy and lack of π-participation. As we all know, allylic hydrogen is more active then the normal alkyl hydrogen. We studies y-sp3C-H activaion of Acrylamide Derivatives. It is found that the γ-position C-H bond arylation of the acrylamides can be smoothly achieved and the subsequent double bond shift leads to the formation of β,γ-unsaturated amide products. The α-and/or β-regioisomeric arylation products are not detected in this transformation. Meanwhile, we have studied the reaction mechanism carefully, it will be helpful for understanding this kind of chemistry.
1.2-亚砜吡啶导向Pd(OAc)2催化的C-H烯基化及芳基化反应研究
近年来,过渡金属催化的引导C-H活化得到了很好的发展,但其也存在一些问题,如引导基难以从产物中移除。因此这两年可移除的引导基也陆续被报导。我们采用2-亚砜吡啶为导向基,研究了在Pd(OAc)2催化下的芳基C-H烯基化及芳基化反应。研究表明,该体系中各种烯烃能够对取代的芳烃进行选择性C-2直接烯基化,产率从中等到良好。另外,也可以直接由简单的芳烃双C-H活化芳基化。特别是2-亚砜吡啶导向基可以通过选择性还原的方法既可以移除也可以转化成其它官能团,从而实现了我们预期的目标。
2.硫醚基团导向Pd(OAc)2催化的C-H键烯基化反应研究
硫醚是有机化合物中重要的结构单元,其在天然产物和药物中都广泛存在,同时在配位化学中也有广泛应用。我们研究了Pd(OAc)2催化的硫醚导向C-H键烯基化反应。产率从中等到良好,并且该反应具有区域选择性和立体选择性,一步生成(E)-异构体的2-位取代产物。并且在烯基化后,硫醚导向基可以在还原条件下移除或保留硫醚导向基团而还原双键：另外还可以选择性氧化成亚砜或砜,从而为进一步官能化提供了可能。
3. Pd(OAc)2催化丙烯酰胺类化合物Y位sp3C-H芳基化反应研究
虽然近年来sp3C-H官能化反应陆续被报道,但由于烷烃C-H键具有较高的活化能并且没有π电子的参与,因此非活性sp3C-H官能化仍是有机合成中的难点。我们知道,烯丙型的C-H键比孤立的sp3C-H键有更强的酸性,因此,我们对内烯酰胺类化合物γ位sp3C-H活化进行了研究。研究发现,在Pd(OAc)2催化下,膦配体作用时,芳基卤化物能够很好地对烯丙位C-H键进行芳基化,并且在芳基卤化物的位阻调配下,可以顺利地选择性进行双芳基化或单芳基化反应。产物中的双键发生了迁移,并且没有观察到α或β芳基化的副产物。同时,我们也对反应机理进行了比较深入的研究,为更深入了解sp3C-H官能化反应提供了依据。
For its ability of coordinating to nitrogen and oxygen, palladium have been becoming the most efficient catalyst for the directing C-H activation. Nowadays, O-containing and N-containing directing groups assisted C-H activation reaction catalyzed by palladium have been widely studied. In despite of this advance, to search the easily transformable, easily removable or newly tape of directing groups still the hot topic in directed C-H activation reaction currently.
This dissertation mainly focused on the studies of palladium catalyzed C-H bond activation assisted by the easily removable and transformable directing groups, which include:
1. Pd(OAc)2-catalyzed C-H alkenylatin and arylation of arenes assisted by removable2-pyridylsulfinyl Group
Nowadays, palladium-catalyzed chelation-directed C-H activation has been widely researched. However, in some cases the practicality might be restricted when the directing groups cannot easily be removed from the products. Therefore, significant effort has been directed toward the discovery of efficient and removable directing groups currently. We studied Pd(OAc)2-catalyzed C-H alkenylation and arylation of arenes assisted by removable2-pyridylsulfinyl group. It was found that a variety of alkenes selectively undergo the direct alkenylation in moderate to good yields. More importantly, this transformation could also be applied in arylation through dual C-H activation with simple arenes. Finally, as we expected, the2-pyridylsulfinyl group could be removed easily after the C-H bond functionalization under reductive conditions or afford diverse reduction products.
2. Pd(OAc)2-catalyzed C-H alkenylatin of arenes using thioether as directing groups
Thioether is an important structural motif in a wide range of molecules with numerous and important applications. It exists in drugs and natural product. It also has been widely used as coordination groups with various metals in many useful complexes. We studied Pd(OAc)2-catalyzed C-H alkenylation of arenes using thioether as directing groups. It was found that the alkenylation could undergo smoothly in moderate to good yields when using thioether as the directing group. It could obtain good regioselective and stereoselective. In most cases, the (E)-isomers were isolated as the major products; and the double alkenylated product can also be obtained with some special substrates. Finally, the alkenylated thioethers can be easily removed and transformed into a variety of useful groups.
3. Pd(OAc)2-catalyzed Regioselective y-Mono-and Diarylation of Acrylamide Derivatives with Aryl Halides
For the past several years, some examples about sp3C-H activation have been reported. But C(sp3)-H bond activation remains a challenging problem because of its high bond dissociation energy and lack of π-participation. As we all know, allylic hydrogen is more active then the normal alkyl hydrogen. We studies y-sp3C-H activaion of Acrylamide Derivatives. It is found that the γ-position C-H bond arylation of the acrylamides can be smoothly achieved and the subsequent double bond shift leads to the formation of β,γ-unsaturated amide products. The α-and/or β-regioisomeric arylation products are not detected in this transformation. Meanwhile, we have studied the reaction mechanism carefully, it will be helpful for understanding this kind of chemistry.
引文
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