title: Palladium-Catalyzed Desilylative Acyloxylation of Silicon-Carbon Bonds on (Trimethylsilyl)arenes: Synthesis of Phenol Derivatives from Trimethylsilylarenes.
abstract: 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.
authors.affiliation: Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University , Honjo-machi, Saga 840-8502, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Gondo
authors.affiliation: Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University , Honjo-machi, Saga 840-8502, Japan.
authors.forename: Juzo
authors.initials: J
authors.lastname: Oyamada
authors.affiliation: Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University , Honjo-machi, Saga 840-8502, Japan.
authors.forename: Tsugio
authors.initials: T
authors.lastname: Kitamura