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Related Concept Videos

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.
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...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
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.
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.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Efficient Pd-catalyzed amination reactions for heterocycle functionalization.

Jaclyn L Henderson1, Stephen L Buchwald

  • 1Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge Massachusetts 02139, USA.

Organic Letters
|September 24, 2010
PubMed
Summary
This summary is machine-generated.

Palladium-catalyzed amination enables efficient modification of unprotected benzo-fused heterocycles. This method offers flexibility for synthesizing diverse molecular structures.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Heterocyclic Chemistry

Background:

  • Benzo-fused heterocycles are crucial scaffolds in medicinal chemistry and materials science.
  • Modifying these structures often requires protecting groups, limiting synthetic flexibility.
  • Developing efficient, direct functionalization methods is highly desirable.

Purpose of the Study:

  • To report a novel palladium-catalyzed amination reaction for unprotected benzo-fused heterocycles.
  • To establish a flexible and efficient method for modifying these important molecular frameworks.
  • To demonstrate the broad applicability of the developed procedure.

Main Methods:

  • Utilized palladium catalysis for the direct amination of unprotected benzo-fused heterocycles.
  • Employed various amine coupling partners and heterocyclic substrates.
  • Optimized reaction conditions for efficiency and yield.

Main Results:

  • Successfully achieved palladium-catalyzed amination of a range of unprotected benzo-fused heterocycles.
  • Demonstrated high functional group tolerance and broad substrate scope.
  • Synthesized diverse structural types with good to excellent yields.

Conclusions:

  • Developed a versatile and efficient Pd-catalyzed amination protocol for unprotected benzo-fused heterocycles.
  • This method significantly enhances flexibility in modifying these key molecular structures.
  • The procedure provides a valuable tool for accessing diverse heterocyclic compounds.