Mechanistic insights into the palladiumII-catalyzed hydroxyalkoxylation of 2-allylphenols |
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Authors: | Thiery Emilie Chevrin Carole Le Bras Jean Harakat Dominique Muzart Jacques |
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Institution: | Unité Mixte de Recherche "Réactions Sélectives et Applications", Bo?te no. 44, CNRS-Université de Reims Champagne-Ardenne, BP 1039, 51687 Reims cedex 2, France. |
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Abstract: | 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. |
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