银催化重氮酯与苯胺,亚胺的三组分反应

doi:10.1016/S1872-2067(18)63088-8

催化学报 ›› 2018, Vol. 39 ›› Issue (10): 1594-1598.DOI: 10.1016/S1872-2067(18)63088-8

银催化重氮酯与苯胺,亚胺的三组分反应

陈佰灵^a,b, 王振^a, 张有灿^a, 赵志刚^b, 陈自立^a

a 中国人民大学化学系, 北京 100872;
b 西南民族大学化学与环境保护工程学院, 四川成都 610041

收稿日期:2018-03-26 修回日期:2018-04-23 出版日期:2018-10-18 发布日期:2018-08-03
通讯作者: 赵志刚, 陈自立
基金资助:
国家自然科学基金（21472237）.

Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine

Bai-Ling Chen^a,b, Zhen Wang^a, You-Can Zhang^a, Zhi-Gang Zhao^b, Zili Chen^a

a Department of Chemistry, Renmin University of China, Beijing 100872, China;
b College of Chemistry & Environment Protection Engineering, Southwest University for Nationalities, Chengdu 610041, Sichuan, China

Received:2018-03-26 Revised:2018-04-23 Online:2018-10-18 Published:2018-08-03
Contact: 10.1016/S1872-2067(18)63088-8
Supported by:
This work was supported by the National Natural Science Foundation of China (21472237).

摘要/Abstract

摘要：

过渡金属催化重氮化合物的卡宾转移反应是有机合成反应的重要研究对象.在这一类反应中，包括环丙烷化、X-H（X=C，N，O，Si，S）插入以及羰基/亚胺叶立德环加成等反应得到了广泛的研究.2003年，胡文浩和Doyle课题组报道了一种新型的反应，即亚胺捕获看似不稳定的氨基叶立德中间体，合成具有高非对映选择性的1，2-二胺化合物.之后，他们又报道了一系列有关氨基叶立德和氧叶立德的研究，与不同的捕获剂，如酮，醛，β，γ-不饱和α羰基羧酸酯和偶氮二酸酸酯等发生反应，生成多种多样的产物类型，基本上都是采用Rh（Ⅲ）催化剂.迄今为止，没有采用其他类型的过渡金属催化剂的报道.
最近，本课题组研究发现，银盐可以作为重氮化合物卡宾转移反应的催化剂，实现了重氮化合物与醛的[2+1]环加成反应合成环氧乙烷类化合物，及重氮化合物与醛、炔/烯三组分的[2+2+1]环加成反应合成二氢呋喃/四氢呋喃类化合物，在这些反应中，加入不同的配体可以调节Ag（I）催化剂的催化活性，从而实现不同的反应过程.基于此，本文将探索Ag（I）做催化剂催化重氮化合物与芳基胺及亚胺的三组分反应合成一系列1，2-二胺类化合物.
研究发现，采用AgOTf/双噁唑啉配体配体作为催化剂组合，可以顺利地实现Ag（I）催化重氮酯、芳基胺及亚胺的三组分反应.尝试了不同的配体，包括膦配体、卡宾配体以及双噁唑啉配体，最后发现，双噁唑啉配体配位的Ag（I）催化反应的效果最好，极大地提高了Ag（I）催化剂的催化活性，其具体的作用机理值得进一步研究.反应中，Ag（I）催化剂的Lewis酸性对二胺产物的非对映选择性有较大的影响.其中，在对硝基苯基亚胺的反应中，产物的非对映选择性很高，大于铑催化反应的结果；而在其他类型亚胺的反应中，反应的非对映选择性较差.另一方面，由于Ag（I）的Lewis酸性，反应过程中发生亚胺与芳基胺的氨基交换反应，从而导致氨基交换的二胺副产物的生成.本文对不同反应底物的各种效应进行了比较详细的研究.

关键词: 银催化, 卡宾转移反应, 三组分反应, 铵基叶立德, 二胺化合物

Abstract:

A new method was developed to diastereoselectively synthesize polysubstituted 1,2-diamine compounds from the reaction of diazoesters with arylamines and diaryl imines by using the dioxazoline ligand L₂-ligated silver catalyst. The Lewis acidity of the silver catalyst affected the different types of substrate diastereoselectivities; It also led to the formation of amine-exchange side products.

Key words: Silver catalysis, Carbene transfer reaction, Three-component reaction, Ammonium ylide, Diamine compouds

陈佰灵, 王振, 张有灿, 赵志刚, 陈自立. 银催化重氮酯与苯胺,亚胺的三组分反应[J]. 催化学报, 2018, 39(10): 1594-1598.

Bai-Ling Chen, Zhen Wang, You-Can Zhang, Zhi-Gang Zhao, Zili Chen. Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine[J]. Chinese Journal of Catalysis, 2018, 39(10): 1594-1598.

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银催化重氮酯与苯胺,亚胺的三组分反应

Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine

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