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Ruthenium-catalyzed redox-neutral and single-step amide synthesis from alcohol and nitrile with complete atom economy

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Title: Ruthenium-catalyzed redox-neutral and single-step amide synthesis from alcohol and nitrile with complete atom economy

Subject: Atom economy, ; N-heterocyclic, ; Nitrogen atom, ; Ruthenium catalysts, ; Single-step, ; Cyanides, ; Isotopes, ; Organic compounds, ; Ruthenium, ; Ruthenium compounds, ; Synthesis (chemical), ; Amides, ; alcohol, ; amide, ; carbene, ; hydrocinnamonitrile, ; nitrile, ; phenethyl alcohol, ; ruthenium, ; unclassified drug, ; amidation, ; article, ; catalysis, ; catalyst, ; chemical bond, ; chemical modification, ; isotope labeling, ; oxidation reduction reaction, ; proton nuclear magnetic resonance, ; synthesis, ; Alcohols, ; Amides, ; Methane, ; Nitriles, ; Oxidation-Reduction, ; Ruthenium

Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.135, no.32, pp.11704 - 11707

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