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Amide Synthesis by Transamidation of Primary Carboxamides

Abstract : The amide functionality is one of the most important and widely used groups in nature and in medicinal and industrial chemistry. Because of its importance and as the actual synthetic methods suffer from major drawbacks, such as the use of a stoichiometric amount of an activating agent, epimerization and low atom economy, the development of new and efficient amide bond forming reactions is needed. A number of greener and more effective strategies have been studied and developed. The transamidation of primary amides is particularly attractive in terms of atom economy and as ammonia is the single byproduct. This review summarizes the advancements in metal-catalyzed and organocatalyzed transamidation methods. Lewis and Bronsted acid transamidation catalysts are reviewed as a separate group. The activation of primary amides by promoter, as well as catalyst- and promoter-free protocols, are also described. The proposed mechanisms and key intermediates of the depicted transamidation reactions are shown.
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Soumis le : vendredi 18 mars 2022 - 17:58:29
Dernière modification le : mardi 27 septembre 2022 - 04:39:42

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Maria Kolympadi Markovic, Dean Markovic, Sylvain Laclef. Amide Synthesis by Transamidation of Primary Carboxamides. Synthesis: Journal of Synthetic Organic Chemistry, Georg Thieme Verlag, 2020, 52 (21), pp.3231-3242. ⟨10.1055/s-0040-1707133⟩. ⟨hal-03613832⟩

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