ORGANIC CHEMISTRY Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation

Nitriles and alkenes are important synthetic intermediates with complementary reactivity that play a central role in the preparation of materials, pharmaceuticals, cosmetics, and agrochemicals. Here, we report a nickel-catalyzed transfer hydrocyanation reaction between a wide range (60 examples) of alkyl nitriles and alkenes. This strategy not only overcomes the toxicity challenge posed by the use of HCN in traditional approaches, but also encompasses distinct chemical advances, including retro-hydrocyanation and anti-Markovnikov regioselectivity. In a broader context, this work highlights an approach to the reversible hydrofunctionalization of alkenes through thermodynamically controlled transfer reactions to circumvent the use of volatile and hazardous reagents in the laboratory.