From this week's C&EN, a method to conduct hydrocyanation without using hydrogen cyanide and--bonus!--with reversibility:
Xianjie Fang, Peng Yu, and Bill Morandi of the Max Planck Institute for Coal Research use a nickel catalyst as a shuttle to pluck hydrogen and a cyano group from a donor nitrile and transfer them to an alkene to form a nitrile. The team shows the reaction is useful to make aryl nitriles and for functionalizing biomolecules such as tyrosine and estrone.
In addition, the transfer hydrocyanation is made reversible on demand by selecting starting reagents that control the thermodynamic equilibrium of the reaction-the nitriles can be reverted to complementary alkenes. The team uses this retrohydrocyanation to make styrene, terpene, and aliphatic alkene derivatives from nitriles.
The paper is in Science, DOI: 10.1126/science.aae0427.
Credit: C&EN