Synthesis 2013; 45(3): 370-374
DOI: 10.1055/s-0032-1316838
paper
© Georg Thieme Verlag Stuttgart · New York

A New Method for the Benzylic Oxidation of Alkylarenes Catalyzed by Hypervalent Iodine(III)

Yuan Xu
College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, P. R. of China   Fax: +86(571)88320238   eMail: jieyan87@zjut.edu.cn
,
Zhenping Yang
College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, P. R. of China   Fax: +86(571)88320238   eMail: jieyan87@zjut.edu.cn
,
Jiantao Hu
College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, P. R. of China   Fax: +86(571)88320238   eMail: jieyan87@zjut.edu.cn
,
Jie Yan*
College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, P. R. of China   Fax: +86(571)88320238   eMail: jieyan87@zjut.edu.cn
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Publikationsverlauf

Received: 09. November 2012

Accepted after revision: 04. Dezember 2012

Publikationsdatum:
03. Januar 2013 (online)


Abstract

A convenient and simple procedure is described for the oxidation of the benzylic C–H moiety of alkylarenes to give the corresponding aryl ketones, using tert-butyl hydroperoxide and m-chloroperoxybenzoic acid in the presence of a catalytic amount of the hypervalent iodine reagent, (diacetoxyiodo)benzene. The reactions typically occur in good yields in 2,2,2-trifluoroethanol as the solvent and at room temperature.