Related Experiment Video
Updated: Sep 13, 2025

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
Published on: October 19, 2017
Reductive Amination Reactions Using Sodium Hypophosphite: a Guide to Substrates
Artemy R Fatkulin1,2, Vasily A Korochantsev1,2, Evgeniya S Podyacheva1,2
1National Research University Higher School of Economics, Myasnitskaya Str. 20, Moscow 101000, Russian Federation.
None:
The reactions of reductive amination are of paramount importance as tools of synthetic organic chemistry. Recently, the applicability of sodium hypophosphite as a promising reductant for such reactions has been demonstrated. However, the limited set of substrates used in those works does not allow for a reliable evaluation of the versatility of the approach for synthesizing amines from starting materials of different natures. Herein, we report a comprehensive study of using NaH2PO2 in the catalyst-free reductive amination. Reaction conditions suitable for various combinations of different classes of amines and carbonyl compounds have been discovered, and limitations of the process have been revealed. The study includes reaction kinetics elucidation, and the relationship between amine nucleophilicity and the outcome of this reaction has been established.
More Related Videos
08:46Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia
When dissolved in liquid ammonia, an alkali metal,...
Nitriles to Amines: LiAlH4 Reduction
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Preparation of Amines: Reduction of Amides and Nitriles
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...