Palladium-Catalyzed Cyanation of Arenediazonium Tetrafluoroborate Derivatives with 2-(Piperidin-1-yl)acetonitrile as the Cyano Source

Abstract

AbstractThe present study describes the one-pot palladium-catalyzed cyanation of commercially available aryldiazonium tetrafluoroborate derivatives with 2-(piperidin-1-yl)acetonitrile (an organic cyano reagent) under mild conditions. This process utilizes a Pd/(Me3Si)2 system and is applied to a wide scope of aromatic diazonium substrates to give the corresponding nitrile-containing products in moderate to high yields (59–92%). This methodology is employed for the preparation of etravirine, a drug used for the treatment of HIV, and for transformations of 1H-indole-2-carbonitrile into compounds that are used as a NMDA receptor antagonists and that have high potential against mutant HIV strains. The mechanism proposed for this Pd-catalyzed cyanation involves cyanide ions, as confirmed using indicator paper.