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Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

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 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: 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,...

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Electrophilic Amination with Nitroarenes.

Marian Rauser¹, Christoph Ascheberg¹, Meike Niggemann¹

¹Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52072, Aachen, Germany.

Angewandte Chemie (International Ed. in English)

|July 21, 2017

Summary

This summary is machine-generated.

A new method converts nitroarenes into alkylated aromatic aminoboranes using zinc organyl compounds. This electrophilic amination offers a direct route from nitro compounds to valuable aminoborane reagents.

Keywords:

aminoboranes boron electrophilic amination nitrenoids nitroarenes

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Nitroarenes are common starting materials in organic synthesis.
Aminoboranes are versatile synthetic intermediates.
Existing methods for aminoborane synthesis can be inefficient.

Purpose of the Study:

To develop a general and direct method for synthesizing alkylated aromatic aminoboranes.
To utilize readily available nitroarenes as precursors.
To establish an alternative to traditional dehydrocoupling methods.

Main Methods:

A two-step partial reduction of nitroarenes to a nitrenoid intermediate.
In situ generation and reaction of the nitrenoid with zinc organyl compounds.
Electrophilic trapping of the resulting air- and moisture-sensitive aminoboranes.

Main Results:

Successful synthesis of alkylated aromatic aminoboranes from nitroarenes.
Demonstration of the method's generality with various electrophiles.
The developed nitrenoid intermediate acts as an effective electrophilic amination reagent.

Conclusions:

The developed method provides a direct transformation of nitroarenes into electrophilic amination reagents.
This approach offers an elegant and efficient alternative to dehydrocoupling for aminoborane generation.
The synthesis of air- and moisture-sensitive aminoboranes is facilitated through electrophilic trapping.