Ruthenium-Catalyzed Redox-Neutral and Single-Step Amide Synthesis from Alcohol and Nitrile with Complete Atom Economy

Abstract

A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrite is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the alpha-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single by-product. A utility of the reaction was demonstrated by synthesizing C-13 or N-15 isotope-labeled amides without involvement of any separate reduction and oxidation step.