Issue 80, 2024

Organoboron catalysis for direct amide/peptide bond formation

Abstract

Amides and peptides are ubiquitous functional groups found in several natural and artificial materials, and they are essential for the advancement of life and material sciences. In particular, their relevance in clinical medicine and drug discovery has increased in recent years. Dehydrative condensation of readily available carboxylic acids with amines is the most “direct” method for amide synthesis; however, this methodology generally requires a stoichiometric amount of condensation agent (coupling reagent). Catalytic direct dehydrative amidation has become an “ideal” methodology for synthesizing amides from the perspective of green chemistry, with water as the only byproduct in principle, high atom efficiency, environmentally friendly, energy saving, and safety. Conversely, organoboron compounds, such as boronic acids, which are widely used in various industries as coupling reagents for Suzuki–Miyaura cross-coupling reactions or pharmaceutical structures, are environmentally friendly molecules that have low toxicity and are easy to handle. Based on the chemical properties of organoboron compounds, they have potential Lewis acidity and the ability to form reversible covalent bonds with dehydration, making them attractive as catalysts. This review explores studies on the development of direct dehydrative amide/peptide bond formation reactions from carboxylic acids using organoboron catalysis, classifying them based on chemical bonding and catalysis over approximately 25 years, from the early developmental days to 2023.

Graphical abstract: Organoboron catalysis for direct amide/peptide bond formation

Article information

Article type
Feature Article
Submitted
20 6 2024
Accepted
02 8 2024
First published
28 8 2024
This article is Open Access
Creative Commons BY license

Chem. Commun., 2024,60, 11202-11222

Organoboron catalysis for direct amide/peptide bond formation

M. Koshizuka, N. Takahashi and N. Shimada, Chem. Commun., 2024, 60, 11202 DOI: 10.1039/D4CC02994A

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