4.4 Article

Transfer Hydration of Dinitriles to Dicarboxamides

Journal

SYNLETT
Volume 30, Issue 17, Pages 1977-1980

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690026

Keywords

hydration; nitriles; palladium; amides; diamides

Funding

  1. Japan Society for the Promotion of Science (JSPS KAKENHI) [JP17K05859]
  2. Toyota Physical and Chemical Research Institute (Toyota Riken)

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We present a robust method for double transfer hydration of dinitriles to afford diamides. The transfer hydration of 1,n-dinitriles (n=1-6) proceeds smoothly in the presence of a palladium(II) catalyst with acetamide as a water donor, affording the corresponding diamides in moderate to high yields, without involving significant side reactions such as monohydration or cyclization. The equilibrium was shifted in the forward direction by removing coproduced acetonitrile under reduced pressure.

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