InCl_3参与的有机反应研究
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摘要
本文主要是对InCl3作为Lewis酸催化剂参与的缩合反应和亲核取代反应方面进行了研究。论文主要是分为三部分论述。
1.本文综述了InCl3在有机合成中作为催化剂的最新研究和应用,对InCl3作为催化剂参与的各种类型的有机反应作了比较详细的归类,并对其作用机制和应用方面进行了比较全面的文献总结。
2.在InCl3催化下,对甲苯磺酰胺和芳香醛,在苯中回流反应,得到芳基磺酰亚胺。此反应操作简单,反应条件温和,对水和空气都不敏感,并且除了芳环上直接连有两个给电子基团的芳香醛与对甲苯磺酰胺缩合的产率只有72%外,其它的产率都高达90%以上。这为芳基磺酰亚胺的合成提供了一个简单有效的新方法。
3.在三氯化铟-硼氢化钠-乙腈体系中,端基炔烃和芳基或烷基磺酰氯反应生成了一系列的α,β-不饱和砜,产率为36-80%。在这个反应中三氯化铟和硼氢化钠在乙腈于-15℃下首先形成氢化二氯化铟,然后氢化二氯化铟再和端基炔烃反应生成烯基铟中间体,最后烯基铟中间体和对甲苯磺酰氯在室温下发生亲核取代反应,得到α,β-不饱和砜。这个反应具有反应条件温和、操作简单及高的区域及立体选择性等特点。
Indium trichloride as a Lewis acid catalyst involved in the condensation reaction and nucleophilic substitution reaction are studied in this paper. It is divided into three parts.
1. In this paper, we review the latest research and application of Indium trichloride as a catalyst in organic synthesis and classify the various types of organic reactions which indium trichloride participated as a catalyst in detail. And its possible mechanism and applications have been summarized comprehensively in the literature.
2. A new method for preparation of N-tosylimines by InCl3-mediated condensation of aldehydes with p-toluenesulfonamide in refluxing benzene has been found. The reaction operation is simple and reaction condition is mild. The yields are up to 90%, but the aromatic aldehydes connecting two electron-donating groups give the desired product in only 72% yield. This is a facile method for synthesis of N-tosylimine.
3. In InCl3-NaBH4-CH3CN system, the aryl terminal alkynes can undergo nucleophilic substitution with aryl-or akryl-sulfonyl chloride and convert intoα,β-unsaturated sulfones. The yields are 36-80%. In this procedure, the reaction of InCl3 with NaBH4 in CH3CN at-15℃gave HInCl2, followed by the reaction with terminal alkynes to generate vinylindium intermediate. And then the reaction of the vinylindium intermediate with aryl-or arkyl-sulfonyl chloride at room temperature affordedα,β-unsaturated sulfones. This new method has several advantages, such as mild reaction conditions, simple experimental process, highly regio-and stereoselectively.
1.本文综述了InCl3在有机合成中作为催化剂的最新研究和应用,对InCl3作为催化剂参与的各种类型的有机反应作了比较详细的归类,并对其作用机制和应用方面进行了比较全面的文献总结。
2.在InCl3催化下,对甲苯磺酰胺和芳香醛,在苯中回流反应,得到芳基磺酰亚胺。此反应操作简单,反应条件温和,对水和空气都不敏感,并且除了芳环上直接连有两个给电子基团的芳香醛与对甲苯磺酰胺缩合的产率只有72%外,其它的产率都高达90%以上。这为芳基磺酰亚胺的合成提供了一个简单有效的新方法。
3.在三氯化铟-硼氢化钠-乙腈体系中,端基炔烃和芳基或烷基磺酰氯反应生成了一系列的α,β-不饱和砜,产率为36-80%。在这个反应中三氯化铟和硼氢化钠在乙腈于-15℃下首先形成氢化二氯化铟,然后氢化二氯化铟再和端基炔烃反应生成烯基铟中间体,最后烯基铟中间体和对甲苯磺酰氯在室温下发生亲核取代反应,得到α,β-不饱和砜。这个反应具有反应条件温和、操作简单及高的区域及立体选择性等特点。
Indium trichloride as a Lewis acid catalyst involved in the condensation reaction and nucleophilic substitution reaction are studied in this paper. It is divided into three parts.
1. In this paper, we review the latest research and application of Indium trichloride as a catalyst in organic synthesis and classify the various types of organic reactions which indium trichloride participated as a catalyst in detail. And its possible mechanism and applications have been summarized comprehensively in the literature.
2. A new method for preparation of N-tosylimines by InCl3-mediated condensation of aldehydes with p-toluenesulfonamide in refluxing benzene has been found. The reaction operation is simple and reaction condition is mild. The yields are up to 90%, but the aromatic aldehydes connecting two electron-donating groups give the desired product in only 72% yield. This is a facile method for synthesis of N-tosylimine.
3. In InCl3-NaBH4-CH3CN system, the aryl terminal alkynes can undergo nucleophilic substitution with aryl-or akryl-sulfonyl chloride and convert intoα,β-unsaturated sulfones. The yields are 36-80%. In this procedure, the reaction of InCl3 with NaBH4 in CH3CN at-15℃gave HInCl2, followed by the reaction with terminal alkynes to generate vinylindium intermediate. And then the reaction of the vinylindium intermediate with aryl-or arkyl-sulfonyl chloride at room temperature affordedα,β-unsaturated sulfones. This new method has several advantages, such as mild reaction conditions, simple experimental process, highly regio-and stereoselectively.
引文
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