过渡金属催化饱和碳上的成键反应
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摘要
过渡金属催化的烷基亲电试剂参与的偶联反应,由于直接涉及饱和碳为中心的成键反应,是现代有机合成中构建复杂分子的重要方法。本论文首先在第一章主要综述了镍催化烷基亲电试剂参与的偶联反应的历史和现状。之后简要介绍了铜、钯、铁、钴催化的烷基亲电试剂参与偶联反应的最新进展。从而得出结论：过渡金属催化烷基亲电试剂和亲核试剂的偶联反应,虽然目前已经有不少报道,但是还存在很多挑战。特别是二级烷基亲电试剂参与的反应还较少,亲核试剂主要是碳亲核试剂,末端炔烃直接作为亲核试剂难以参与反应等。
针对亲核试剂主要是为碳亲核试剂的问题,在第二章中我们发展了使用硼作为新型亲核试剂的烷基Miyaura反应。首次实现了钯催化一级烷基亲电试剂的Miyaura反应。但是钯无法实现二级烷基亲电试剂的硼化反应。于是我们实现了首例镍催化的二级烷基亲电试剂的Miyaura反应。和我们组报道的铜催化的烷基硼化反应相比,钯催化的反应具有更好的化学选择性,只和一级的烷基亲电试剂反应。镍催化的硼化反应和铜相比,具有非常明显的配体效应。Fu小组发展了一系列镍催化二级烷基亲电试剂的不对称碳碳键成键反应。由于镍催化硼化反应中配体是必须的,这就为通过配体来控制不对称碳硼键的生成提供了特殊的机会。我们对镍催化不对称硼化反应做了些尝试。钯催化的硼化反应可能经历了SN2的反应历程,而镍催化的硼化反应可能经历了自由基的反应历程。
针对末端炔烃作为亲核试剂无法和二级烷基亲电试剂发生偶联反应的问题,我们发展了首例镍催化二级烷基亲电试剂的Sonogashira反应(第3章)。我们使用位阻较小的Pybox类的三齿氮配体,能够顺利地实现一、二级烷基卤代物和末端炔烃的偶联反应。新反应避免使用了前人工作中用到的烷基金属试剂、炔基亲电试剂或炔基金属试剂等难以获得的原料。这个反应对于带取代基的环状亲电试剂有很好的非对映选择性,产物以热力学稳定的构象为主,并且得到单晶结构的证明。使用我们的新方法能够方便地对一些具有生理活性的分子进行进一步的衍生化,TMS保护的末端炔也可以实现双烷基化。我们认为这个反应经历了自由基反应历程。我们对三级烷基亲电试剂也进行了尝试,但是主要得到了炔烃自身氧化偶联的产物,三级烷基亲电试剂可能扮演了氧化剂的角色。
Transition metal-catalyzed cross-coupling reactions which involving alkyl electrophiles, as directly concerned about the saturated carbon bond formation reaction, has emerged as an important method in modern organic synthesis. In chapter one, the history and current status of Ni catalyzed cross-coupling of alkyl electrophiles is summarized. After a brief update on the recent progress of copper, palladium, iron, cobalt catalyzed cross coupling reaction involving alkyl electrophilic reagent, we come to the the conclusion that although there have been numerous reports about transition metal-catalyzed coupling reactions with alkyl electrophiles and nucleophiles, but there are still many challenges. The reactions concerned about secondary alkyl electrophiles are still rare. The uncleophiles are limited to carbon atom. And the terminal alkynes can not react with the secondary electrophiles.
For the problem of unclephiles is limited to carbon atom. In chapter two, we developed a novel use of boron as unclophile in alkyl Miyaura reaction. We reported the first Pd catalyzed primary alkyl Miyaura reaction. However, Pd could not achieve the borylation of secondary alkyl electrophiles. Then we reported the first Ni catalyzed secondary alkyl Miyaura reaction. Compared with the former report of Cu catalyzed borylation by our group, the Pd catalyzed reaction had better chemical selectivity, which only primary alkyl halide was reacted. The Ni catalyzed borylation had a distinct ligand effort compared with Cu. Fu group had developed a serie of Ni catalyzed asymmetric carbon-carbon bond-forming reactions by secondary alkyl electrophiles. Since the ligand was required, this gave us a unique opportunity to control the asymmetric of the carbon-boron bond. We also made some attempts to Ni catalyzed asymmetric carbon-boron bond formation. The Pd catalyzed borylation might involve an SN2mechanism and the Ni catalyzed borylation might involve a free radical mechanism.
For the problem of terminal alkynes could not react with secondary alkyl electrophiles. In chapter three, we first reported the Ni catalyzed Sonogashira reactions with secondary electrophiles. A less hindered tridentate nitrogen ligand of Pybox was used to achieve a smooth coupling reaction of secondary alkyl electrophile with terminal alkyne. The new report avoided the use of alkyl metal reagents, alkynyl electrophiles or alkynyl metal reagents which were wildly used but were difficult to attach by the previous reports. The reaction had good diastereoselectivity of cyclic substituted alkyl electrophiles, and the products were mainly in a thermodynamically stable conformation. And we further evidenced by a single crystal. Some biologically active molecules could be conveniently further derivatized; the TMS-caped alkyne could achieve double alkylation. After preliminary studies into the mechanism, we believed that this reaction also experienced a radical mechanism. The tertiary alkyl electrophiles were also tested, but the main products were the dimeric oxidative coupling of alkynes. The tertiary alkyl electrophiles might play the role of oxidant.
针对亲核试剂主要是为碳亲核试剂的问题,在第二章中我们发展了使用硼作为新型亲核试剂的烷基Miyaura反应。首次实现了钯催化一级烷基亲电试剂的Miyaura反应。但是钯无法实现二级烷基亲电试剂的硼化反应。于是我们实现了首例镍催化的二级烷基亲电试剂的Miyaura反应。和我们组报道的铜催化的烷基硼化反应相比,钯催化的反应具有更好的化学选择性,只和一级的烷基亲电试剂反应。镍催化的硼化反应和铜相比,具有非常明显的配体效应。Fu小组发展了一系列镍催化二级烷基亲电试剂的不对称碳碳键成键反应。由于镍催化硼化反应中配体是必须的,这就为通过配体来控制不对称碳硼键的生成提供了特殊的机会。我们对镍催化不对称硼化反应做了些尝试。钯催化的硼化反应可能经历了SN2的反应历程,而镍催化的硼化反应可能经历了自由基的反应历程。
针对末端炔烃作为亲核试剂无法和二级烷基亲电试剂发生偶联反应的问题,我们发展了首例镍催化二级烷基亲电试剂的Sonogashira反应(第3章)。我们使用位阻较小的Pybox类的三齿氮配体,能够顺利地实现一、二级烷基卤代物和末端炔烃的偶联反应。新反应避免使用了前人工作中用到的烷基金属试剂、炔基亲电试剂或炔基金属试剂等难以获得的原料。这个反应对于带取代基的环状亲电试剂有很好的非对映选择性,产物以热力学稳定的构象为主,并且得到单晶结构的证明。使用我们的新方法能够方便地对一些具有生理活性的分子进行进一步的衍生化,TMS保护的末端炔也可以实现双烷基化。我们认为这个反应经历了自由基反应历程。我们对三级烷基亲电试剂也进行了尝试,但是主要得到了炔烃自身氧化偶联的产物,三级烷基亲电试剂可能扮演了氧化剂的角色。
Transition metal-catalyzed cross-coupling reactions which involving alkyl electrophiles, as directly concerned about the saturated carbon bond formation reaction, has emerged as an important method in modern organic synthesis. In chapter one, the history and current status of Ni catalyzed cross-coupling of alkyl electrophiles is summarized. After a brief update on the recent progress of copper, palladium, iron, cobalt catalyzed cross coupling reaction involving alkyl electrophilic reagent, we come to the the conclusion that although there have been numerous reports about transition metal-catalyzed coupling reactions with alkyl electrophiles and nucleophiles, but there are still many challenges. The reactions concerned about secondary alkyl electrophiles are still rare. The uncleophiles are limited to carbon atom. And the terminal alkynes can not react with the secondary electrophiles.
For the problem of unclephiles is limited to carbon atom. In chapter two, we developed a novel use of boron as unclophile in alkyl Miyaura reaction. We reported the first Pd catalyzed primary alkyl Miyaura reaction. However, Pd could not achieve the borylation of secondary alkyl electrophiles. Then we reported the first Ni catalyzed secondary alkyl Miyaura reaction. Compared with the former report of Cu catalyzed borylation by our group, the Pd catalyzed reaction had better chemical selectivity, which only primary alkyl halide was reacted. The Ni catalyzed borylation had a distinct ligand effort compared with Cu. Fu group had developed a serie of Ni catalyzed asymmetric carbon-carbon bond-forming reactions by secondary alkyl electrophiles. Since the ligand was required, this gave us a unique opportunity to control the asymmetric of the carbon-boron bond. We also made some attempts to Ni catalyzed asymmetric carbon-boron bond formation. The Pd catalyzed borylation might involve an SN2mechanism and the Ni catalyzed borylation might involve a free radical mechanism.
For the problem of terminal alkynes could not react with secondary alkyl electrophiles. In chapter three, we first reported the Ni catalyzed Sonogashira reactions with secondary electrophiles. A less hindered tridentate nitrogen ligand of Pybox was used to achieve a smooth coupling reaction of secondary alkyl electrophile with terminal alkyne. The new report avoided the use of alkyl metal reagents, alkynyl electrophiles or alkynyl metal reagents which were wildly used but were difficult to attach by the previous reports. The reaction had good diastereoselectivity of cyclic substituted alkyl electrophiles, and the products were mainly in a thermodynamically stable conformation. And we further evidenced by a single crystal. Some biologically active molecules could be conveniently further derivatized; the TMS-caped alkyne could achieve double alkylation. After preliminary studies into the mechanism, we believed that this reaction also experienced a radical mechanism. The tertiary alkyl electrophiles were also tested, but the main products were the dimeric oxidative coupling of alkynes. The tertiary alkyl electrophiles might play the role of oxidant.
引文
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