金/钯双金属纳米颗粒协同催化酰胺和醇间氢自转移反应中路易斯酸驱动反应路径

doi:10.1016/S1872-2067(16)62483-X

催化学报 ›› 2016, Vol. 37 ›› Issue (10): 1662-1668.DOI: 10.1016/S1872-2067(16)62483-X

金/钯双金属纳米颗粒协同催化酰胺和醇间氢自转移反应中路易斯酸驱动反应路径

Hiroyuki Miyamura, Satoshi Isshiki, Hyemin Min, Shū Kobayashi

东京大学理学院化学系, 东京113-0033, 日本

收稿日期:2016-04-14 修回日期:2016-06-07 出版日期:2016-10-21 发布日期:2016-10-22
通讯作者: Shū Kobayashi

Lewis acid-driven reaction pathways in synergistic cooperative catalysis over gold/palladium bimetallic nanoparticles for hydrogen autotransfer reaction between amide and alcohol

Hiroyuki Miyamura, Satoshi Isshiki, Hyemin Min, Shū Kobayashi

Department of Chemistry, School of Science, The University of Tokyo, Tokyo 113-0033, Japan

Received:2016-04-14 Revised:2016-06-07 Online:2016-10-21 Published:2016-10-22
Contact: Shū Kobayashi
Supported by:
This work was partially supported by a Grant-in-Aid for Science Research from the Japan Society for the Promotion of Science (JSPS), the Global COE Program, the University of Tokyo, the Japan Science and Technology Agency (JST), and the Ministry of Education, Culture, Sports, Science and Technology (MEXT, Japan).

摘要/Abstract

摘要：

金属纳米颗粒，特别是金和它的双金属纳米颗粒作为强大的绿色催化剂广泛用于有机合成反应中.在一个反应体系中使用2个不同催化剂（如协同催化），在均相催化中是一个很好的策略.然而，这种方法仍在发展中.最近我们发现，金/钯双金属纳米颗粒与路易斯酸的协同催化体系可用于伯胺的N-烷基化：即酰胺与醇之间的氢自转移反应.我们详细报道了路易斯酸对该氢自转移反应的影响.结果表明，所选的路易斯酸不仅影响生成目标产物的反应路径，而且影响生成多个中间体和副产物的反应路径.弱的路易斯酸，如三氟甲磺酸碱土金属盐，非常适合酰胺的N-烷基化反应.

关键词: 金, 钯, 双金属纳米颗粒, 路易斯酸, 酰胺合成, 氢自转移

Abstract:

Metal nanoparticle catalysts, especially gold and its bimetallic nanoparticle catalysts, have been widely used in organic transformations as powerful and green catalysts. The concept of employing two distinct catalysts in one reaction system, such as in cooperative and synergistic catalysis, is a powerful strategy in homogeneous catalysis. However, the adaption of such a strategy to metal nanoparticle catalysis is still under development. Recently, we have found that cooperative catalytic systems of gold/palladium bimetallic nanoparticles and Lewis acid can be used for the N-alkylation of primary amides through hydrogen autotransfer reaction between amide and alcohol. Herein, the results of a detailed investigation into the effects of Lewis acids on this hydrogen autotransfer reaction are reported. It was found that the choice of Lewis acid affected not only the reaction pathway leading to the desired product, but also other reaction pathways that produced several intermediates and by-products. Weak Lewis acids, such as alkaline-earth metal triflates, were found to be optimal for the desired N-alkylation of amides.

Key words: Gold, Palladium, Bimetallic nanoparticle, Lewis acid, Amide synthesis, Hydrogen autotransfer

Hiroyuki Miyamura, Satoshi Isshiki, Hyemin Min, Shū Kobayashi. 金/钯双金属纳米颗粒协同催化酰胺和醇间氢自转移反应中路易斯酸驱动反应路径[J]. 催化学报, 2016, 37(10): 1662-1668.

Hiroyuki Miyamura, Satoshi Isshiki, Hyemin Min, Shū Kobayashi. Lewis acid-driven reaction pathways in synergistic cooperative catalysis over gold/palladium bimetallic nanoparticles for hydrogen autotransfer reaction between amide and alcohol[J]. Chinese Journal of Catalysis, 2016, 37(10): 1662-1668.

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金/钯双金属纳米颗粒协同催化酰胺和醇间氢自转移反应中路易斯酸驱动反应路径

Lewis acid-driven reaction pathways in synergistic cooperative catalysis over gold/palladium bimetallic nanoparticles for hydrogen autotransfer reaction between amide and alcohol

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