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: laurent.elkaimensta.fr,
laurence.grimaud
ensta.fr
L. El Kaim, M. Gizolme, L. Grimaud, Org. Lett., 2006, 8, 5021-5023.
DOI: 10.1021/ol0617502
Abstract
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
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