Synthesis of Phenol Derivatives from Trimethylsilylarenes

A strategy for desilylative acetoxylation of (trimethylsilyl)arenes has been developed in which (trimethylsilyl)arenes are converted into acetoxyarenes. The direct acetoxylation is performed in the presence of 5 mol % of Pd(OAc)₂ and PhI(OCOCF₃)₂ (1.5 equiv) in AcOH at 80 °C for 17 h. The acetoxyarenes are obtained in good to high yields (67–98%). The synthetic utility is demonstrated with a one-pot transformation of (trimethylsilyl)arenes to phenols by successive acetoxylation and hydrolysis. Furthermore, desilylative acyloxylation of 2-(trimethylsilyl)naphthalene using several carboxylic acids has been conducted.

标签： Phenol