Novel and Direct Oxidative Cyanation Reactions of Heteroaromatic Compounds Mediated by A Hypervalent Iodine(III) Reagent was written by Dohi, Toshifumi;Morimoto, Koji;Kiyono, Yorito;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Organic Letters in 2005.Application In Synthesis of 3-Methylthiophene-2-carbonitrile This article mentions the following:
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 biol. important pyrroles 2f and 2g. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Application In Synthesis of 3-Methylthiophene-2-carbonitrile).
3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application In Synthesis of 3-Methylthiophene-2-carbonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts