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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...
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...
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 Amines: Reductive Amination of Aldehydes and Ketones01:38

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.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

David S Surry1, Stephen L Buchwald

  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA. ; Tel: +1-617-253-1885.

Chemical Science
|March 21, 2012
PubMed
Summary

This review guides selecting optimal dialkylbiaryl phosphine ligands and reaction conditions for palladium-catalyzed amination. It focuses on practical substrate combinations for efficient synthetic applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Dialkylbiaryl phosphines are crucial ligands in palladium-catalyzed amination reactions.
  • These ligands have broad applicability across various synthetic contexts.
  • Effective ligand and condition selection is key for successful amination.

Purpose of the Study:

  • To provide a guide for selecting appropriate dialkylbiaryl phosphine ligands.
  • To assist in choosing optimal reaction conditions for palladium-catalyzed aminations.
  • To address common and practically important substrate combinations.

Main Methods:

  • Literature review of palladium-catalyzed amination reactions.
  • Analysis of substrate scope and ligand performance.
  • Compilation of recommended ligand-substrate pairings and conditions.

Main Results:

  • Identification of key dialkylbiaryl phosphine ligands for specific substrate classes.
  • Correlation of ligand structure with catalytic activity and selectivity.
  • Summary of optimized reaction parameters for common amination scenarios.

Conclusions:

  • The judicious selection of dialkylbiaryl phosphines and reaction conditions enhances palladium-catalyzed amination efficiency.
  • This review serves as a practical resource for synthetic chemists.
  • Optimized ligand choice leads to improved outcomes in complex substrate aminations.