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Atom-economic catalytic amide synthesis from amines and carboxylic acids activated in situ with acetylenes

Author

Listed:
  • Thilo Krause

    (FB Chemie-Organische Chemie, Technische Universität Kaiserslautern)

  • Sabrina Baader

    (FB Chemie-Organische Chemie, Technische Universität Kaiserslautern)

  • Benjamin Erb

    (FB Chemie-Organische Chemie, Technische Universität Kaiserslautern)

  • Lukas J. Gooßen

    (FB Chemie-Organische Chemie, Technische Universität Kaiserslautern)

Abstract

Amide bond-forming reactions are of tremendous significance in synthetic chemistry. Methodological research has, in the past, focused on efficiency and selectivity, and these have reached impressive levels. However, the unacceptable amounts of waste produced have led the ACS GCI Roundtable to label ‘amide bond formation avoiding poor atom economy’ as the most pressing target for sustainable synthetic method development. In response to this acute demand, we herein disclose an efficient one-pot amide coupling protocol that is based on simple alkynes as coupling reagents: in the presence of a dichloro[(2,6,10-dodecatriene)-1,12-diyl]ruthenium catalyst, carboxylate salts of primary or secondary amines react with acetylene or ethoxyacetylene to vinyl ester intermediates, which undergo aminolysis to give the corresponding amides along only with volatile acetaldehyde or ethyl acetate, respectively. The new amide synthesis is broadly applicable to the synthesis of structurally diverse amides, including dipeptides.

Suggested Citation

  • Thilo Krause & Sabrina Baader & Benjamin Erb & Lukas J. Gooßen, 2016. "Atom-economic catalytic amide synthesis from amines and carboxylic acids activated in situ with acetylenes," Nature Communications, Nature, vol. 7(1), pages 1-7, September.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms11732
    DOI: 10.1038/ncomms11732
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    Cited by:

    1. Jie Gao & Rui Ma & Fairoosa Poovan & Lan Zhang & Hanan Atia & Narayana V. Kalevaru & Wenjing Sun & Sebastian Wohlrab & Denis A. Chusov & Ning Wang & Rajenahally V. Jagadeesh & Matthias Beller, 2023. "Streamlining the synthesis of amides using Nickel-based nanocatalysts," Nature Communications, Nature, vol. 14(1), pages 1-13, December.

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