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

Keisuke Gondo, Juzo Oyamada and Tsugio Kitamura*

*Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan, Email: kitamuracc.saga-u.ac.jp

K. Gondo, J. Oyamada, T. Kitamura, Org. Lett., 2015, 17, 4778-4781.

DOI: 10.1021/acs.orglett.5b02336 (free Supporting Information)


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Abstract

Desilylative acetoxylation of (trimethylsilyl)arenes can be performed in the presence of 5 mol % of Pd(OAc)2 and PhI(OCOCF3)2 (1.5 equiv) in AcOH at 80C for 17 h providing acetoxyarenes in very good yields. The synthetic utility is demonstrated with a one-pot transformation of (trimethylsilyl)arenes to phenols by successive acetoxylation and hydrolysis.

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Key Words

phenols, PIFA


ID: J54-Y2015