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Related Concept Videos

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
Preparation of 1° Amines: Azide Synthesis01:22

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 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
05:07

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Published on: June 23, 2019

Rapid and efficient access to secondary arylmethylamines.

Nicolas Fleury-Brégeot1, Jessica Raushel, Deidre L Sandrock

  • 1Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 7, 2012
PubMed
Summary

New ammoniomethyl trifluoroborates enable Suzuki-Miyaura cross-couplings for secondary amines. This advances access to biologically relevant aryl- and heteroaryl-methylamine motifs, complementing existing methods for primary and tertiary amines.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Suzuki-Miyaura cross-coupling is vital for synthesizing biologically relevant motifs.
  • Previous methods using ammoniomethyl trifluoroborates were limited to primary and tertiary amines.

Purpose of the Study:

  • To develop a method for synthesizing secondary ammoniomethyl trifluoroborates.
  • To establish efficient Suzuki-Miyaura cross-coupling conditions for these new reagents.

Main Methods:

  • One-step nucleophilic substitution on potassium bromomethyltrifluoroborate to synthesize secondary ammoniomethyltrifluoroborates.
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling using an aminobiphenyl precatalyst with aryl bromides.

Main Results:

  • Successfully synthesized a diverse range of secondary ammoniomethyltrifluoroborates.
  • Achieved efficient coupling of these trifluoroborates with aryl bromides under mild conditions.

Conclusions:

  • This work expands the utility of ammoniomethyl trifluoroborates in organic synthesis.
  • Provides access to all three classes of aminomethylarenes (primary, secondary, and tertiary) via cross-coupling reactions.