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Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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 Amines: Reduction of Amides and Nitriles

Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...

Nitriles to Amines: LiAlH4 Reduction

Nitriles to Amines: LiAlH₄ Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
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...

Amides to Amines: LiAlH4 Reduction

Amides to Amines: LiAlH₄ Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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...

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Reductive amination using cobalt-based nanoparticles for synthesis of amines.

Kathiravan Murugesan¹, Vishwas G Chandrashekhar¹, Thirusangumurugan Senthamarai¹

¹Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Rostock, Germany.

Nature Protocols

|March 24, 2020

Summary

This study introduces novel cobalt-based nanoparticle catalysts for reductive amination, offering a sustainable and cost-effective alternative to precious metals. These catalysts efficiently synthesize diverse amines, including valuable pharmaceutical compounds.

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Area of Science:

Catalysis
Organic Synthesis
Materials Science

Background:

Reductive amination is vital for synthesizing amines and pharmaceuticals.
Current catalysts (precious metals, Raney nickel) have limitations.
Development of base-metal catalysts is key for sustainable processes.

Purpose of the Study:

To develop efficient, cost-effective, and sustainable base-metal nanostructured catalysts for reductive amination.
To prepare carbon-supported cobalt-based nanoparticles as alternative catalysts.

Main Methods:

Template synthesis of a cobalt-triethylenediamine-terephthalic acid metal-organic framework on carbon.
Pyrolysis to create supported single cobalt atoms and nanoparticles.
Catalytic reductive amination using synthesized cobalt catalysts.

Main Results:

Successfully synthesized carbon-supported cobalt nanoparticles and single atoms.
Demonstrated efficient synthesis of diverse primary, secondary, and tertiary amines.
Achieved synthesis of pharmaceutically relevant amine products.

Conclusions:

Cobalt-based nanostructured catalysts are effective for reductive amination.
This method provides a sustainable and economical alternative to traditional catalysts.
The catalysts enable the synthesis of a wide range of valuable amine compounds.