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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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Publication details

The article was received on 20 Sep 2010, accepted on 22 Nov 2010 and first published on 18 Jan 2011


Article type: Paper
DOI: 10.1039/C0OB00749H
Citation: 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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