Mechanistic Insights into the
PalladiumII-Catalyzed Hydroxyalkoxylation of
2-Allylphenols

Thiery, Emilie; Chevrin, Carole; Bras, Jean Le; Harakat, Dominique; Muzart, Jacques

doi:10.1021/jo062491x.s002

Mechanistic Insights into the Palladium^II-Catalyzed Hydroxyalkoxylation of 2-Allylphenols

journal contribution

posted on 2007-03-02, 00:00 authored by Emilie Thiery, Carole Chevrin, Jean Le Bras, Dominique Harakat, Jacques Muzart

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.