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

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

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

Received Date: 14 April 2016
Revised Date: 7 June 2016

Fund Project: 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).

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.
- Gold,
- Palladium,
- Bimetallic nanoparticle,
- Lewis acid,
- Amide synthesis,
- Hydrogen autotransfer
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