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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

Supporting Info

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 togo@scichem.s.chiba-u.ac.jp

J. Org. Chem., 2003, 68 (16), pp 6424–6426

DOI: 10.1021/jo030045t

Publication Date (Web): July 11, 2003

†

Graduate School of Science and Technology.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

‡

Department of Chemistry.

Abstract

α-Tosyloxyketones and α-tosyloxyaldehydes were directly prepared from alcohols by treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate in good yields. This method can be used for the direct preparation of thiazoles, imidazoles, and imidazo[1,2-a]pyridines from alcohols in good to moderate yields by the successive treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate, followed by thioamides, benzamidine, and 2-aminopyridine, respectively.

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