Environmentally Benign Ritter Reaction Using Bismuth Salts as a Catalyst

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.

This is the peer-reviewed version of the following article: Ueno, M. , Kusaka, R. , Ohmura, S. D. and Miyoshi, N. (2019), Environmentally Benign Ritter Reaction Using Bismuth Salts as a Catalyst. Eur. J. Org. Chem., 2019: 1796-1800, which has been published in final form at https://doi.org/10.1002/ejoc.201801882. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.