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
Key words primary amides - transamidation - amide bond - carboxamides - amine formylation
