A hassle-free and cost-effective transfer hydrogenation strategy for the chemoselective reduction of arylnitriles to primary amines through in situ-generated nickelII dihydride intermediate in water

• Published in: Journal of molecular structure 2022-05, Vol.1255, p.131926, Article 131926
• Main Authors: Zeynizadeh, Behzad, Mousavi, Hossein, Mohammad Aminzadeh, Farkhondeh
• Format: Article
• Language: English
• Subjects: Chemoselective; Green solvent; Ni(OAc)2•4H2O; NickelII dihydride; Primary amine; Reduction of nitrile; Transfer hydrogenation; Water solvent
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.131926

•Green reaction medium (use of water solvent).•High chemoselectivity.•Use of available materials for one of the important organic transformation.•Reduction (or hydrogenation) process has done via in situ-generated nickelII dihydride intermediate.•Ni2B-free trajectory.•Good-to-excellent yields of the desired products.•Relatively short reaction times.•Base- and ligand-free protocol.•Cost-effective and convenient synthetic protocol.•Easy work-up procedure. In this paper, we have introduced a new, simple, efficient, inexpensive, and chemoselective transfer hydrogenation strategy for the straightforward reduction of arylnitriles to corresponding primary amines using sodium borohydride (NaBH4) and nickel acetate tetrahydrate (Ni(OAc)2•4H2O) through in situ-generated nickelII dihydride intermediate in the water medium at 50 ᵒC. The presented methodology features moderate reaction conditions, nickel boride (Ni2B)-free trajectory, good-to-excellent yields of the products, relatively short reaction times, satisfactory chemoselectivity, and does not involve the use of toxic organic solvent and also any base or ligand. [Display omitted]