Palermo AF,
Chiu BS. Y,
Patel P,
Rousseaux SA. L.
*
University of Toronto, Canada
Nickel-Catalyzed Reductive Alkyne Hydrocyanation Enabled by Malononitrile and a Formaldehyde Additive.
J. Am. Chem. Soc. 2023;
145: 24981-24989
Key words
alkynes - hydrocyanation - malononitriles - nickel catalysis - transnitrilation
Significance
Rousseaux and co-workers disclosed a nickel-catalyzed alkyne hydrocyanation making use of glycolonitrile as active cyanating agent, which is formed in situ by reductive coupling of 2-methyl-2-phenylmalononitrile (MPMN) and formaldehyde.
Comment
The proposed mechanism is supported by mechanistic studies such as deuterium labeling and anion trapping experiments, ruling out the generation of a nickel-hydride intermediate.
