Nickel-catalyzed Reductive Hydrolysis of Nitriles to Alcohols.

Autor: Jagadeesh RV; Leibniz-Institut fur Katalyse eV, Catalysis for Sustainable Syntheses, Albert-Einstein-Straße 29A, 18059, Rostock, GERMANY., Kuloor C; Leibniz Institute for Catalysis, Catalysis for Sustainable Syntheses, GERMANY., Goyal V; VSB-Technical University of Ostrava, Materials Env Lab, CZECHIA., Zbořil R; VSB-Technical University of Ostrava, Materials EnV Lab, CZECHIA., Beller M; Leibniz Institute for Catalysis, Applied Homogeneous Catalysis, GERMANY., Akash A; Leibniz Institute for Catalysis, Catalysis for Sustainable Syntheses, GERMANY.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Dec 06, pp. e202414689. Date of Electronic Publication: 2024 Dec 06.
DOI: 10.1002/anie.202414689
Abstrakt: Nitriles are an abundant class of compounds that are widely used as versatile feedstocks to produce various chemicals including pharmaceuticals, and agrochemicals as well as materials. Here we report Ni-catalyzed reductive hydrolysis of nitriles to alcohols in the presence of molecular hydrogen. This conversion likely occurs in a domino reaction sequence that first involves the hydrogenation of nitrile to primary imine, then the hydrolysis of imine, and subsequent deamination to the aldehyde, which is finally hydrogenated to the desired alcohol. Crucial for this reductive hydrolysis process is the commercially available triphos-ligated Ni-complex that enables highly efficient and selective transformation of aromatic, heterocyclic, and aliphatic nitriles including fatty nitriles to prepare functionalized primary alcohols. Further, the synthetic applicability of this Ni-based protocol is presented for the selective conversion of nitrile to 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 energy technologies.
(© 2024 Wiley‐VCH GmbH.)
Databáze: MEDLINE