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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,...

Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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...

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,...

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Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

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Breaking Amides using Nickel Catalysis.

Jacob E Dander¹, Neil K Garg¹

¹Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.

|June 20, 2017

Summary

This summary is machine-generated.

Nickel catalysis enables new amide C-N bond activation for esterification, transamidation, and coupling reactions. This expands the synthetic utility of amides as versatile building blocks in organic synthesis.

Keywords:

amides catalysis cross-coupling nickel nonprecious metal

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Amides are ubiquitous functional groups but their synthetic utility is limited by challenges in C-N bond activation.
Traditional methods for amide C-N bond cleavage are often harsh or inefficient.

Purpose of the Study:

To develop novel catalytic methods for activating the amide C-N bond.
To expand the synthetic applications of amides in organic transformations.

Main Methods:

Nickel-catalyzed reactions were employed for amide C-N bond activation.
Key transformations investigated include esterification, transamidation, Suzuki-Miyaura coupling, and Negishi coupling.

Main Results:

Demonstrated successful esterification and transamidation reactions utilizing amides as starting materials.
Achieved Suzuki-Miyaura and Negishi couplings via amide C-N bond activation.
Established amides as versatile synthons for constructing C-heteroatom and C-C bonds.

Conclusions:

Nickel catalysis provides a powerful platform for amide C-N bond activation.
These new methodologies significantly enhance the synthetic utility of amides.
The findings are expected to promote broader use of amides in multi-step synthesis and organic chemistry research.