Environmentally Benign Ritter Reaction Using Bismuth Salts as a Catalyst

作者：Masaharu Ueno, Ryo Kusaka, Satoshi D. Ohmura, Norikazu Miyoshi · 发表于：European Journal of Organic Chemistry · 年份：2019 · DOI：10.1002/ejoc.201801882 · 被引用次数：23 · 研究领域：Chemical Synthesis and Reactions、Chemical Synthesis and Analysis、Asymmetric Hydrogenation and Catalysis

We developed an environmentally benign Ritter reaction of alcohols with nitriles using a commercially available bismuth salt as a less harmful catalyst. The detailed reaction profiles revealed that consumption of the ether by‐product as the reaction proceeded was the key for optimizing this reaction, and the yield of the target amide was improved by adding a small amount of water. This finding clearly reveals the significance of using a bismuth salt as the catalyst, as it is not deactivated in the presence of water. This catalyst system has a broad substrate scope, and even with 1 mol‐% of the catalyst, the reaction progresses smoothly. It is also possible to react stoichiometric amounts of nitriles and alcohols, thus reducing the amount of organic solvent required for the reaction. Furthermore, as the inexpensive bismuth catalyst can be easily removed using aqueous hydrochloric acid, a purification process that only required washing and drying without any organic solvents was successfully established.