Novel and Direct Oxidative Cyanation Reactions of Heteroaromatic Compounds Mediated by A Hypervalent Iodine(III) Reagent

Abstract

The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) mediates the selective cyanation reactions of a wide range of electron-rich heteroaromatic compounds such as pyrroles, thiophenes, and indoles under mild conditions. These reactions proceed via a cation radical intermediate, and the key for the successful transformation presumably depends on the oxidation-reduction potential of the substrates used. The synthetic utility has been demonstrated through the conversion of these biologically important pyrroles 2f and 2g. [reaction: see text]