Nickel-catalyzed reductive hydrolysis of nitriles to alcohols

Abstract

Nitriles are an abundant class of compounds that are widely used as versatile feedstocks to produce variouschemicals including pharmaceuticals, and agrochemicals as well as materials. Here we report Ni-catalyzed reductivehydrolysis of nitriles to alcohols in the presence of molecular hydrogen. This conversion likely occurs in a dominoreaction sequence that first involves the hydrogenation of nitrile to primary imine, then the hydrolysis of imine, andsubsequent deamination to the aldehyde, which is finally hydrogenated to the desired alcohol. Crucial for this reductivehydrolysis process is the commercially available triphos-ligated Ni-complex that enables highly efficient and selectivetransformation of aromatic, heterocyclic, and aliphatic nitriles including fatty nitriles to prepare functionalized primaryalcohols. Further, the synthetic applicability of this Ni-based protocol is presented for the selective conversion of nitrileto alcoholic group in structurally diverse and complex drug molecules as well as agrochemicals. The resulting products,alcohols are indispensable chemicals commonly used in organic synthesis and life sciences as well as material and energytechnologies.