Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation

Abstract

A route to nitrile that bypasses cyanide The toxicity of hydrogen cyanide (HCN) is well known. Nonetheless, numerous useful nitrile compounds contain CN groups, and the reaction of HCN with C=C double bonds is often used. Fang et al. now report an alternative to shuttle a CN group from one molecule to another that relies on Ni and Al catalysts (see the Perspective by Schmalz). This transfer procedure circumvents the need for HCN and can be applied to complex substrates using a simple sacrificial nitrile donor. It can also be run “in reverse” to derive an olefin of interest from a nitrile precursor. Science , this issue p. 832 ; see also p. 817