Mechanistic insights into the palladium(II)-catalyzed hydroxyalkoxylation of 2-allylphenols

作者：Thiery Emilie; Chevrin Carole; Le Bras Jean; Harakat Dominique; Muzart Jacques^*

来源：Journal of Organic Chemistry, 2007, 72(5): 1859-1862.

DOI：10.1021/jo062491x

The Pd(OCOCF3)(2)/[(HOCH2CH2NHCOCH2)(2)NCH2](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 CC bond followed by its epoxidation and oxirane opening led to the products. Recycling of the catalytic system led to gradual lost of activity.

• 出版日期2007-3-2