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Keywords:

  • acrylonitriles;
  • cyanides;
  • domino reactions;
  • iron;
  • propargylic substitution;
  • rearrangement
Thumbnail image of graphical abstract

Nontoxic cyanide source: An unprecedented route to acrylonitriles by employing propargylic alcohols and para-tolylsulfonohydrazide as a combined cyano source has been developed (see scheme). This efficient and practical cyanation reaction proceeds through an FeCl3-catalyzed domino propargylic substitution/aza-Meyer–Schuster rearrangement sequence, the rearrangement process of which is reported for the first time.