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Iodoarene-Mediated α-Tosyloxylation of Ketones with MCPBA and p-Toluenesulfonic Acid

Ayumi Tanaka, Katsuhiko Moriyama, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522 Japan, Email: togofaculty.chiba-u.jp

A. Tanaka, K. Moriyama, H. Togo, Synlett, 2011, 1853-1854.

DOI: 10.1055/s-0030-1260948 (free Supporting Information)


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Abstract

Various ketones could be reacted into α-tosyloxy ketones in the presence of MCPBA, PTSA•H2O, catalytic amounts of iodine and tert-butylbenzene in a mixture of acetonitrile and 2,2,2-trifluoroethanol. In the reaction, 4-tert-butyl-1-iodobenzene is formed at first and then converted into the α-tosyloxylation reagent 4-tert-butyl-1-[(hydroxy)(tosyloxy)iodo]benzene by the reaction with MCPBA and PTSA•H2O.


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PhI-Catalyzed α-Tosyloxylation of Ketones with m-Chloroperbenzoic Acid and p-Toluenesulfonic Acid

Y. Yamamoto, H. Togo, Synlett, 2006, 798-800.


Key Words

molecular iodine, tert-butylbenzene, hypervalent iodine compounds, Koser's Reagent, α-tosyloxy ketones, α-hydroxylation, ketones, m-chloroperbenzoic acid, p-toluenesulfonic acid, catalysts


ID: J60-Y2011-2290