One-pot Reductive Amination of Carbonyl Compounds with NaBH 4 -B(OSO 3 H) 3 /SiO 2 in Acetonitrile and in Solvent-free Condition

Abstract

An efficient one-pot procedure for the direct reductive amination of aldehyde and ketones was achieved in the presence of sodium borohydride by using B(OSO 3 H) 3 /SiO 2 (SBSA) as the reusable solid catalyst in acetonitrile and solvent-free conditions. Both aromatic and aliphatic aldehyde reacted well to give the corresponding amines in excellent yields. All the products are known and well-characterized. The catalyst is recoverable and could be easily recycled by filtration and reused several times without any significant loss of its activity. SBSA acts as a dual Brønsted/Lewis acid that is an air-stable and cost-effective solid acid.

Crystal Structure of a Chiral Sec-Amine, 4-Chloro-N-(1-(pyridin-2-yl)ethyl)aniline

“…A known ligand (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)ethan-1-imine (L a ) [21] was first synthesized using methods similar to our earlier reports [22,23]. Afterward, L a was reduced to a secondary ligand 4-chloro-N-(1-(pyridin-2-yl)ethyl)aniline (L b ) (Scheme 1) using a modified method from the literature [24].…”

Hitchhiker’s Guide to Reductive Amination

“…tones with NaBH 4 can be obtained in good yields using more complicated methods. Process should be conducted in the presence of silica gel-supported sulfuric acid, 35 silicasupported boron sulfonic acid, 36 or silica chloride. 37 Efficiency of the reaction can be improved also by using 2,2,2trifluoroethanol 38 or ionic liquid 39 as solvent.…”

Polyionic Resin Supported Pd/Fe2O3Nanohybrids for Catalytic Hydrodehalogenation: Improved and Versatile Remediation for Toxic Pollutants

“…In hydrodehalogenation reactions, the common hydride sources are mixed metal hydrides, ammonium formate, silane derivatives, and molecular hydrogen. Sodium borohydride (NaBH 4 ) is recognized as a green, efficient, environment-friendly, and safe reducing agent . The use of NaBH 4 has some advantages as it forms hydrogen gas with water or with polar hydroxylic solvents at a faster rate on metal surfaces.…”

“…Sodium borohydride (NaBH 4 ) is recognized as a green, efficient, environmentfriendly, and safe reducing agent. 34 The use of NaBH 4 has some advantages as it forms hydrogen gas with water or with polar hydroxylic solvents at a faster rate on metal surfaces. The homogeneous metallic systems along with NaBH 4 reagent have shown profound effect on HDH reaction, 35,36 and other sources of hydrogen with heterogeneous metals catalysts are known.…”