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

Yukiharu Yamamoto, Hideo Togo*

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

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

DOI: 10.1055/s-2006-933120

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Abstract

Various α-tosyloxyketones were efficiently prepared in high yields from the reaction of ketones with m-chloroperbenzoic acid and p-toluenesulfonic acid in the presence of a catalytic amount of iodobenzene.

see article for more examples

proposed mechanism

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

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

Novel Oxidative α-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid and Its Synthetic Use for Direct Preparation of Heteroaromatics

M. Ueno, T. Nabana, H. Togo, J. Org. Chem., 2003, 68, 6424-6426.

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Key Words

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

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ID: J60-Y2006-4330