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Synthesis 2020; 52(21): 3231-3242
DOI: 10.1055/s-0040-1707133
DOI: 10.1055/s-0040-1707133
special topic
Amide Synthesis by Transamidation of Primary Carboxamides
D.M. would like to thank the Croatian Science Foundation (Hrvatska Zaklada za Znanost) for funding through project IP-2019-04-8846. Furthermore, financial support was provided by the University of Rijeka (research grant UNIRI-prirod-18-102). M.K.M. is grateful to the Croatian Science Foundation for funding her postdoctoral position through the project IP-2016-06-3568.Weitere Informationen
Publikationsverlauf
Received: 16. April 2020
Accepted: 06. Mai 2020
Publikationsdatum:
04. Juni 2020 (online)
Published as part of the Special Topic Recent Advances in Amide Bond Formation
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 Brønsted 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.
1 Introduction
2 Metal-Catalyzed Transamidations
3 Organocatalyzed Transamidations
4 Lewis and Brønsted Acid Catalysis
5 Promoted Transamidation of Primary Amides
6 Catalyst- and Promoter-Free Protocols
7 Conclusion
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