O-arylative Passerini reactions.
The three-component addition of isocyanides to phenol derivatives and aldehydes proceeds easily in methanol to form O-arylated compounds in a new Passerini-type reaction. The key step of the conversion lies in an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts. It represents the first use of a Smiles rearrangement in a Passerini reaction. [reaction: see text]
El Kaim
Laurent
L
Laboratoire Chimie et procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Boulevard Victor, 75739 Paris Cedex 15, France. laurent.elkaim@ensta.fr
Gizolme
Marie
M
Grimaud
Laurence
L