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Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature

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  • Guangchen Li

    (Rutgers University)

  • Michal Szostak

    (Rutgers University)

Abstract

Amide chemistry has an essential role in the synthesis of high value molecules, such as pharmaceuticals, natural products, and fine chemicals. Over the past years, several examples of transamidation reactions have been reported. In general, transition-metal-based catalysts or harsh conditions are employed for these transformations due to unfavorable kinetics and thermodynamics of the process. Herein, we report a significant advance in this area and present the general method for transition-metal-free transamidation of amides and amidation of esters by highly selective acyl cleavage with non-nucleophilic amines at room temperature. In contrast to metal-catalyzed protocols, the method is operationally-simple, environmentally-friendly, and operates under exceedingly mild conditions. The practical value is highlighted by the synthesis of valuable amides in high yields. Considering the key role of amides in various branches of chemical science, we envision that this broadly applicable method will be of great interest in organic synthesis, drug discovery, and biochemistry.

Suggested Citation

  • Guangchen Li & Michal Szostak, 2018. "Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-06623-1
    DOI: 10.1038/s41467-018-06623-1
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    Cited by:

    1. Théo Guérin & Alina Ghinet & Christophe Waterlot, 2020. "Toward a New Way for the Valorization of Miscanthus Biomass Produced on Metal-Contaminated Soils Part 2: Miscanthus-Based Biosourced Catalyst: Design, Preparation, and Catalytic Efficiency in the Synt," Sustainability, MDPI, vol. 13(1), pages 1-12, December.

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