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Issue 5, 2011
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Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)

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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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Supplementary files

Article information


Submitted
20 Sep 2010
Accepted
22 Nov 2010
First published
18 Jan 2011

Org. Biomol. Chem., 2011,9, 1614-1620
Article type
Paper

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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