Barbier型反应体系和PhI（OAc）_2反应体系在胺类转化与合成中的应用
摘要
本论文主要对锌试剂Barbier型条件下胺、亚胺的转化和PhI(OAc)_2/I_2体系下氮杂环丙烷的合成做了一些研究。
第一部分的工作中,我们研究了Barbier型条件下醛,胺,锌粉,溴试剂一锅法的亲核加成反应。这种反应可以高效的得到高苄基和高烯丙基胺类化合物。我们提出了一个六元环中间体来解释这种反应的机理,对其进一步的研究发现对于各种不同的醛和胺这种方法都能够以良好的产率得到产物。
在上述工作的基础上,我们开展了第二部分的工作。在同样的条件下,使用磺酰胺替代普通胺,反应会生成N-磺酰基亚胺。这种方法适用于芳基醛,脂肪醛等各种醛,反应同样适用于叔丁基亚磺酰胺。我们设想这个反应的机理和第一部分的反应类似,经过了一个四元环中间体。
第三部分的工作研究了PhI(OAc)_2/I_2体系在合成氮杂环丙烷中的应用。经过细致的条件优化,实现了存这种体系下以优秀的产率合成氮杂环丙烷。
This thesis focuses on the transformation of amines and imines under the condition of Barbier-type reactions,and also the synthesis of aziridines catalyzed by the PhI(OAc)_2/I_2 system.
In the first part,we studied the nucleophilic addition reactions of aldehyde, amine,Zinc and benzyl bromide in one pot to afford homobenzyl and homoallyl amines in moderate to good yields.Based on the experimental results,a six-member-ring intermediate was proposed as the mechanism for these reactions. Moreover,we found that it can also afford good yields to different aldehydes and amines by using this method.
In the second part,we alternated amines to sulfonamides under the same reaction system and found that N-sulfonyl aldimine was formed.Meanwhile,we discovered that kinds of aldehydes,such as phenyl and acyclic aldehydes,and N-sulfinyl can also give similar results in mild conditions.A four-member-ring intermediate was proposed as the mechanism for these reactions.
In the last part we studied the application of PhI(OAc)_2/I_2 in the synthesis of aziridines.The yield was promoted to be good after the optimization of reaction conditions.
第一部分的工作中,我们研究了Barbier型条件下醛,胺,锌粉,溴试剂一锅法的亲核加成反应。这种反应可以高效的得到高苄基和高烯丙基胺类化合物。我们提出了一个六元环中间体来解释这种反应的机理,对其进一步的研究发现对于各种不同的醛和胺这种方法都能够以良好的产率得到产物。
在上述工作的基础上,我们开展了第二部分的工作。在同样的条件下,使用磺酰胺替代普通胺,反应会生成N-磺酰基亚胺。这种方法适用于芳基醛,脂肪醛等各种醛,反应同样适用于叔丁基亚磺酰胺。我们设想这个反应的机理和第一部分的反应类似,经过了一个四元环中间体。
第三部分的工作研究了PhI(OAc)_2/I_2体系在合成氮杂环丙烷中的应用。经过细致的条件优化,实现了存这种体系下以优秀的产率合成氮杂环丙烷。
This thesis focuses on the transformation of amines and imines under the condition of Barbier-type reactions,and also the synthesis of aziridines catalyzed by the PhI(OAc)_2/I_2 system.
In the first part,we studied the nucleophilic addition reactions of aldehyde, amine,Zinc and benzyl bromide in one pot to afford homobenzyl and homoallyl amines in moderate to good yields.Based on the experimental results,a six-member-ring intermediate was proposed as the mechanism for these reactions. Moreover,we found that it can also afford good yields to different aldehydes and amines by using this method.
In the second part,we alternated amines to sulfonamides under the same reaction system and found that N-sulfonyl aldimine was formed.Meanwhile,we discovered that kinds of aldehydes,such as phenyl and acyclic aldehydes,and N-sulfinyl can also give similar results in mild conditions.A four-member-ring intermediate was proposed as the mechanism for these reactions.
In the last part we studied the application of PhI(OAc)_2/I_2 in the synthesis of aziridines.The yield was promoted to be good after the optimization of reaction conditions.
引文
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