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

Org Biomol Chem. 2011 Mar 7;9(5):1614-20. doi: 10.1039/c0ob00749h. Epub 2011 Jan 18.

Abstract

Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF(3)·OEt(2) 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 BF(3)·OEt(2), the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields.