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

Makoto Ueno, Takahiro Nabana, and Hideo Togo*

*Graduate School of Science and Technology, and Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522 Japan, Email: togoscichem.s.chiba-u.ac.jp

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

DOI: 10.1021/jo030045t


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Abstract

α-Tosyloxyketones and α-tosyloxyaldehydes were directly prepared from alcohols by treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate in good yields. Modified methods gave thiazoles, imidazoles and imidazo[1,2-a]pyridines from alcohols in good to moderate yields.

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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

Iodosylbenzene, α-Hydroxylation, Heterocycles


ID: J42-Y2003-590