Issue 5, 2011
From the journal:

Organic & Biomolecular Chemistry

Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)†

Huan Liu,a   Xuemin Wanga  and  Yonghong Gu*a  

* Corresponding authors

a Department of Chemistry, University of Science and Technology of China, Hefei, China
E-mail: ygu01@ustc.edu.cn
Fax: +86-551-3601592
Tel: +86-551-3602470

Abstract

Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF3·OEt2 in AcOH at room temperature afforded the corresponding para-acetoxylated products with high regioselectivity. In addition, this reaction could be expanded to the etherification of anilides. In the presence of 2.0 equiv. of PIFA and 2.0 equiv. of BF3·OEt2, the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields.

Graphical abstract: Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)

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Article information

DOI
https://doi.org/10.1039/C0OB00749H
Article type
Paper
Submitted
20 Sep 2010
Accepted
22 Nov 2010
First published
18 Jan 2011

Org. Biomol. Chem., 2011,9, 1614-1620

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Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)

H. Liu, X. Wang and Y. Gu, Org. Biomol. Chem., 2011, 9, 1614 DOI: 10.1039/C0OB00749H

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