Synthesis 2013; 45(6): 791-797
DOI: 10.1055/s-0032-1318199
paper
© Georg Thieme Verlag Stuttgart · New York

Iodine-Mediated α-Sulfonyloxylation of Alkyl Aryl Ketones with Oxone® and Sulfonic Acids

Hiroki Kikui
Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan   Email: togo@faculty.chiba-u.jp
,
Katsuhiko Moriyama
Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan   Email: togo@faculty.chiba-u.jp
,
Hideo Togo*
Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan   Email: togo@faculty.chiba-u.jp
› Author Affiliations
Further Information

Publication History

Received: 25 December 2012

Accepted after revision: 20 January 2013

Publication Date:
19 February 2013 (online)


Abstract

Alkyl aryl ketones are converted into the corresponding α-sulfonyloxyketones, in moderate to excellent yields, via a novel procedure that utilizes Oxone®, p-toluenesulfonic acid or methanesulfonic acid and molecular iodine in a mixture of acetonitrile and 2,2,2-trifluoroethanol. The yield is found to be dependent on the nature of the ketone. A mechanism is proposed in which the key intermediates are an α-iodoketone and a subsequently formed α-iodosylketone. The latter reacts with the sulfonic acid to afford the α-sulfonyloxyketone product.