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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.4K
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...
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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...
3.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
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.
3.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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.
2.8K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

2.8K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Tertiary Amides as Directing Groups for Enantioselective C-H Amination using Ion-Paired Rhodium Complexes.

Kieran J Paterson1, Amit Dahiya1, Benjamin D Williams1

  • 1Yusuf Hamied Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.

Angewandte Chemie (International Ed. in English)
|February 13, 2024
PubMed
Summary

This study introduces a new method for creating chiral benzylamines via enantioselective C-H amination. Achiral rhodium catalysts paired with chiral cations enable this transformation with broad substrate scope and excellent ortho-substituent tolerance.

Keywords:
aminationasymmetric catalysischiral cationsnitrenoidrhodium

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Area of Science:

  • Organic Chemistry
  • Asymmetric Catalysis
  • C-H Functionalization

Background:

  • Chiral benzylamines are important synthetic targets.
  • Enantioselective C-H amination offers a direct route to these compounds.
  • Previous methods often require specific substrate functionalization.

Purpose of the Study:

  • To develop a novel enantioselective benzylic C-H amination method.
  • To utilize achiral rhodium catalysts with chiral counterions.
  • To achieve high enantioselectivity with a broad substrate scope.

Main Methods:

  • Employing an achiral anionic Rh complex ion-paired with a Cinchona alkaloid-derived chiral cation.
  • Utilizing tertiary amides (butyric and valeric acid-derived) as substrates.
  • Investigating the role of directing groups and substrate interactions.

Main Results:

  • Achieved highly enantioselective benzylic amination of tertiary amides.
  • Demonstrated broad substrate scope, including various arene substitutions and amide types.
  • Observed excellent tolerance of ortho substituents, a significant advancement.
  • Identified methyl ethers as effective directing groups.

Conclusions:

  • The developed method provides an efficient route to chiral benzylamines.
  • The catalytic system shows remarkable substrate tolerance and scope.
  • Hydrogen bonding interactions between substrate and chiral cation are crucial for selectivity.
  • The discovery of methyl ether directing groups expands the applicability of the catalyst system.