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

Thilo Krause, Sabrina Baader, Benjamin Erb and Lukas J. Gooßen ()
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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

Nature Communications, 2016, vol. 7, issue 1, 1-7

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms11732

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