Palladium-Catalyzed Desilylative Acyloxylation of Silicon鈥揅arbon Bonds on (Trimethylsilyl)arenes: Synthesis of Phenol Derivatives from Trimethylsilylarenes

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• 作者：Keisuke Gondo ; Juzo Oyamada ; Tsugio Kitamura
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：October 2, 2015
• 年：2015
• 卷：17
• 期：19
• 页码：4778-4781
• 全文大小：327K
• ISSN：1523-7052

文摘

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 掳C for 17 h. The acetoxyarenes are obtained in good to high yields (67鈥?8%). 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.