Mechanistic insights into the palladiumII-catalyzed hydroxyalkoxylation of 2-allylphenols.
The Pd(OCOCF3)2/[(HOCH2CH2NHCOCH2)2NCH2]2-catalyzed oxidation of o-allylphenol with H2O2 in water/methanol affords a syn and anti mixture of 2-(1,2-dihydroxypropyl)phenol and 2-(2-hydroxy-1-methoxypropyl)phenol. Mechanistic experiments and ESI-MS studies support a pathway wherein isomerization of the C=C bond followed by its epoxidation and oxirane opening led to the products. Recycling of the catalytic system led to gradual lost of activity.
Thiery
Emilie
E
Unité Mixte de Recherche "Réactions Sélectives et Applications", Boîte no. 44, CNRS-Université de Reims Champagne-Ardenne, BP 1039, 51687 Reims cedex 2, France.
Chevrin
Carole
C
Le Bras
Jean
J
Harakat
Dominique
D
Muzart
Jacques
J