4.6 Article

Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 17, Pages 5894-5898

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600234

Keywords

amides; amines; boronic acid; synthetic methods; transamidation

Funding

  1. ANR NeoACAT [ANR-JC-12]
  2. Labex SynOrg [ANR-11-LABX-0029]
  3. region Normandie

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A highly efficient and mild transamidation of amides with amines co-catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral alpha-amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron-derived Lewis acidity rather than an improved Bronsted acidity of acetic acid.

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