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Related Concept Videos

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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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,...
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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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.
7.7K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

13.1K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Enantioselective Aromatic Amination?

Vinzenz Thönnißen1, Frederic W Patureau1

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 19, 2020
PubMed
Summary

Enantioselective C-N bond formation, crucial for asymmetric synthesis, remains challenging despite advances. This work explores the difficulties and presents new methods for atroposelective amination reactions.

Keywords:
Buchwald-HartwigChan-LamUllmann-Goldbergatroposelective aminationenantioselective amination

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Catalysis

Background:

  • Amination reactions are fundamental in organic synthesis.
  • Traditional methods like Gabriel, Ullmann, Goldberg, Buchwald, and Hartwig couplings lack enantioselectivity.
  • Asymmetric synthesis is a well-established field, yet enantioselective C-N bond formation is notably underdeveloped.

Purpose of the Study:

  • To investigate the challenges hindering enantioselective C-N bond formation.
  • To discuss the reasons behind the limited success in this area.
  • To introduce emerging solutions and paradigm shifts in atroposelective amination.

Main Methods:

  • Review of existing amination reaction methodologies.
  • Analysis of factors contributing to the difficulty of enantioselective C-N bond formation.
  • Discussion of novel catalytic systems and strategies for atroposelective synthesis.

Main Results:

  • Identified key challenges in achieving high enantioselectivity in C-N bond formation.
  • Highlighted the scarcity of enantioselective methods compared to other coupling reactions.
  • Presented initial examples of promising new approaches to atroposelective amination.

Conclusions:

  • Enantioselective C-N bond formation presents unique synthetic hurdles.
  • Despite difficulties, recent advancements suggest a potential paradigm shift in atroposelective amination.
  • Further research is needed to fully realize the potential of these new methods.