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Synthesis 2012(8): 1226-1232  
DOI: 10.1055/s-0031-1289750
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel One-Pot Method for α-Tosyloxylation of Ketones Using a Catalytic Amount of Ammonium Iodide

Jiantao Hua, Min Zhub, Yuan Xua, Jie Yan*a
a College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, P. R. of China
Fax: +86(571)88320238; e-Mail: jieyan87@zjut.edu.cn;
b College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, P. R. of China
Further Information

Publication History

Received 14 January 2012
Publication Date:
15 March 2012 (online)

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Abstract

A novel one-pot procedure was designed for the preparation of various α-tosyloxy ketones in good yields by the reaction of ketones with m-chloroperoxybenzoic acid and p-toluenesulfonic acid monohydrate in the presence of catalytic amounts of ammonium iodide and benzene in a mixture of acetonitrile and 2,2,2-trifluo­roethanol (8:2) at room temperature for 24 hours.

Key words

α-tosyloxylation - α-tosyloxy ketones - hypervalent iodine intermediate - ammonium iodide

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