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

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.