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Chem Sci. 2020 Apr 30;11(25):6500-6509. doi: 10.1039/d0sc01349h. eCollection 2020 Jul 07.

Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents.

Chemical science

Michael Fairley, Leonie J Bole, Florian F Mulks, Laura Main, Alan R Kennedy, Charles T O'Hara, Joaquín García-Alvarez, Eva Hevia

Affiliations

  1. Department of Pure and Applied Chemistry , University of Strathclyde Glasgow , G1 1XL , UK.
  2. Department für Chemie und Biochemie , Universität Bern , CH3012 , Bern , Switzerland . Email: [email protected].
  3. Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC) , Centro de Innovación en Química Avanzada (ORFEO-CINQA) , Departamento de Química Orgánica e Inorgánica (IUQOEM) , Facultad de Química , Universidad de Oviedo , E-33071 , Oviedo , Spain.

PMID: 32874519 PMCID: PMC7441706 DOI: 10.1039/d0sc01349h

Abstract

Lithium amides constitute one of the most commonly used classes of reagents in synthetic chemistry. However, despite having many applications, their use is handicapped by the requirement of low temperatures, in order to control their reactivity, as well as the need for dry organic solvents and protective inert atmosphere protocols to prevent their fast decomposition. Advancing the development of air- and moisture-compatible polar organometallic chemistry, the chemoselective and ultrafast amidation of esters mediated by lithium amides is reported. Establishing a novel sustainable access to carboxamides, this has been accomplished

This journal is © The Royal Society of Chemistry 2020.

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