钯催化剂在催化氢化和水相反应中的应用
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摘要
发展高效、高选择性的有机反应和寻找环境友好的合成方法,已经成为有机化学研究的重要内容。对金属催化有机反应的研究日益引起人们的兴趣,其中对金属钯作为高效催化剂的研究最为热门。本论文研究了金属钯催化剂在有机合成中的应用。内容主要集中在两个方面,一是Pd/C催化的化学选择性氢化反应,二是钯试剂催化的水相有机反应。
Pd/C作为一种最传统的钯催化剂,在催化氢化方面有着广泛地应用。论文系统地研究了Pd/C催化氢化还原活性苯甲醛成相应甲苯的方法,首次提出了缩醛反应机理。在酸性条件下以甲醇或乙醇做溶剂催化氢化还原活性苯甲醛时,反应首先是苯甲醛和甲醇或乙醇形成缩醛,然后通过两次碳氧键的氢解得到相应的甲苯。通过简单地在传统的Pd/C催化体系中加入氯仿,即可建立起一个活性自调节的Pd/C催化体系。利用氯仿在Pd/C催化氢化条件下去氯氢化原位产生氯化氢对Pd/C催化剂催化活性的调节,实现了芳香醛的直接还原胺化反应。用该方法能够减少芳香醛直接催化还原胺化过程中的副反应,而且产物以盐酸盐的形成直接从体系中方便地分离出来。最后,还提出了一个新颖的四步催化循环机理。
在论文的第4章中,设计和合成了二醛肟配体并探讨了它在Suzuki反应中的应用。利用该配体,成功地实现了水相中氯苯和溴苯的Suzuki反应,反应只需要0.1 mol%的催化剂。由于该配体能够和钯形成双核的配合物,比普通的醛肟具有更高的催化活性。催化剂具有很高的TON值,在经过4次原位循环反应后,催化剂还能够保持较高的活性。
论文研究了水相条件下不同还原剂在钯催化的卤代芳烃的自身偶联反应中的应用,通过对比发现葡萄糖作为还原剂具有较好的反应效果。同时还发现,使用相转移催化剂可以显著提高反应的产率。该反应可以在无配体的条件下进行,无论溴代苯和溴代杂芳环均能取得较高的产率。
Development of highly efficient and selective reactions was an important part in modern organic chemistry. Catalytic reactions, especially the palladium catalyzed reactions, most attracted our attention. In this thesis, the application of palladium catalysts in organic synthesis were studies mainly focusing on two aspects. One is the chemical selectivity of the Pd/C catalyst in catalytic hydrogenations, the other is the application of palladium catalyst in aqueous reaction.
As a traditional palladium catalyst, Pd/C was widely used in catalytic hydrogenation. In chapter 2, the catalytic hydrogenolysis of benzaldehydes to methylbenzenes was studied. A three stage novel‘acetal pathway’was first revealed by a systematic study when lower alcohols were used as solvents. In the first stage, benzaldehyde carried out an acetalization catalyzed by aq. HCl and Pd/C together to yield dimethyl acetal. Then, dimethyl acetal carried out a Pd/C catalyzed“fast hydrogenolysis”to give the benzyl methyl ether. Finally, benzyl methyl ether underwent a Pd-C catalyzed“slow hydrogenolysis”to give methylbenzene. A solvent-controlled highly efficient procedure for hydrogenolysis of benzaldehydes to methylbenzenes was established.
In chapter 3, by adding a few milliliters of CHCl3 in the conventional Pd/C catalytic hydrogenation condition, a self-adjusted system was established. Using this system, an unprecedented efficient and chemoselective DRA of benzaldehydes and primary amines was developed to directly yield N-substituted benzylamine hydrochlorides as single products in practically quantitative yields. A four-stage cyclic pathway was proposed.
In chapter 4, a group of dioxime ligands were designed and synthesized. The ligands may form dinuclear complexes with palladium, by that a novel aqueous Suzuki coupling between halobenenzes and phenylboronic acids was catalyzed efficiently. The catalyst had a very high TON with very low loading (0.1 mol%) and can be recycled four times in suit without significant lose of the reactivity.
In chapter 5, the aqueous homocoupling of bromoarenes was studied systematically by using different reducing agents. As a result, we found that glucose is the most efficient reducing agent and the phase transfer catalyst played a very important role in the coupling reaction. When phase transfer catalyst was used, the yield of the homocoupling was improved. The homocoupling reaction was carried out using palladium diacetate as catalyst without any ligand. Both bromopyridines and bromobenzenes can give good results.
Pd/C作为一种最传统的钯催化剂,在催化氢化方面有着广泛地应用。论文系统地研究了Pd/C催化氢化还原活性苯甲醛成相应甲苯的方法,首次提出了缩醛反应机理。在酸性条件下以甲醇或乙醇做溶剂催化氢化还原活性苯甲醛时,反应首先是苯甲醛和甲醇或乙醇形成缩醛,然后通过两次碳氧键的氢解得到相应的甲苯。通过简单地在传统的Pd/C催化体系中加入氯仿,即可建立起一个活性自调节的Pd/C催化体系。利用氯仿在Pd/C催化氢化条件下去氯氢化原位产生氯化氢对Pd/C催化剂催化活性的调节,实现了芳香醛的直接还原胺化反应。用该方法能够减少芳香醛直接催化还原胺化过程中的副反应,而且产物以盐酸盐的形成直接从体系中方便地分离出来。最后,还提出了一个新颖的四步催化循环机理。
在论文的第4章中,设计和合成了二醛肟配体并探讨了它在Suzuki反应中的应用。利用该配体,成功地实现了水相中氯苯和溴苯的Suzuki反应,反应只需要0.1 mol%的催化剂。由于该配体能够和钯形成双核的配合物,比普通的醛肟具有更高的催化活性。催化剂具有很高的TON值,在经过4次原位循环反应后,催化剂还能够保持较高的活性。
论文研究了水相条件下不同还原剂在钯催化的卤代芳烃的自身偶联反应中的应用,通过对比发现葡萄糖作为还原剂具有较好的反应效果。同时还发现,使用相转移催化剂可以显著提高反应的产率。该反应可以在无配体的条件下进行,无论溴代苯和溴代杂芳环均能取得较高的产率。
Development of highly efficient and selective reactions was an important part in modern organic chemistry. Catalytic reactions, especially the palladium catalyzed reactions, most attracted our attention. In this thesis, the application of palladium catalysts in organic synthesis were studies mainly focusing on two aspects. One is the chemical selectivity of the Pd/C catalyst in catalytic hydrogenations, the other is the application of palladium catalyst in aqueous reaction.
As a traditional palladium catalyst, Pd/C was widely used in catalytic hydrogenation. In chapter 2, the catalytic hydrogenolysis of benzaldehydes to methylbenzenes was studied. A three stage novel‘acetal pathway’was first revealed by a systematic study when lower alcohols were used as solvents. In the first stage, benzaldehyde carried out an acetalization catalyzed by aq. HCl and Pd/C together to yield dimethyl acetal. Then, dimethyl acetal carried out a Pd/C catalyzed“fast hydrogenolysis”to give the benzyl methyl ether. Finally, benzyl methyl ether underwent a Pd-C catalyzed“slow hydrogenolysis”to give methylbenzene. A solvent-controlled highly efficient procedure for hydrogenolysis of benzaldehydes to methylbenzenes was established.
In chapter 3, by adding a few milliliters of CHCl3 in the conventional Pd/C catalytic hydrogenation condition, a self-adjusted system was established. Using this system, an unprecedented efficient and chemoselective DRA of benzaldehydes and primary amines was developed to directly yield N-substituted benzylamine hydrochlorides as single products in practically quantitative yields. A four-stage cyclic pathway was proposed.
In chapter 4, a group of dioxime ligands were designed and synthesized. The ligands may form dinuclear complexes with palladium, by that a novel aqueous Suzuki coupling between halobenenzes and phenylboronic acids was catalyzed efficiently. The catalyst had a very high TON with very low loading (0.1 mol%) and can be recycled four times in suit without significant lose of the reactivity.
In chapter 5, the aqueous homocoupling of bromoarenes was studied systematically by using different reducing agents. As a result, we found that glucose is the most efficient reducing agent and the phase transfer catalyst played a very important role in the coupling reaction. When phase transfer catalyst was used, the yield of the homocoupling was improved. The homocoupling reaction was carried out using palladium diacetate as catalyst without any ligand. Both bromopyridines and bromobenzenes can give good results.
引文
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