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O-Arylative Passerini Reactions

Laurent El Kaïm*, Marie Gizolme, Laurence Grimaud*

*Laboratoire de Chimie Organique, UMR CNRS 7652, Ecole Nationale Supérieure des Techniques Avancées, 32 Bd Victor, 75015, Email:,

L. El Kaim, M. Gizolme, L. Grimaud, Org. Lett., 2006, 8, 5021-5023.

DOI: 10.1021/ol0617502


A three-component addition of isocyanides to phenol derivatives and aldehydes in methanol forms O-arylated compounds in a new Passerini-type reaction. The key step is an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts.

see article for more examples

proposed mechanism

Phenol Ugi-Smiles Systems: Strategies for the Multicomponent N-Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols

L. El Kaim, L. Grimaud, J. Oble, Angew. Chem. Int. Ed., 2005, 44, 7961-7964.

Key Words

amines, arylation, multicomponent reaction, phenols, rearrangement, Passerini reaction, Smiles rearrangement

ID: J54-Y2006-3400