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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.1K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
11.9K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.2K
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...
4.2K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.1K
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...
4.1K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.5K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.5K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.5K
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...
6.5K

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Updated: Oct 5, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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A Perspective on Late-Stage Aromatic C-H Bond Functionalization.

Li Zhang1, Tobias Ritter1

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany.

Journal of the American Chemical Society
|January 27, 2022
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Summary

Late-stage functionalization of C-H bonds offers efficient synthesis of complex molecules. This perspective evaluates aromatic C-H LSF challenges and strategies for reactivity, selectivity, and scope.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Late-stage functionalization of C-H bonds (C-H LSF) is a powerful synthetic strategy.
  • C-H LSF enables efficient synthesis of complex molecules.
  • Challenges remain in achieving selectivity in the presence of diverse functional groups.

Purpose of the Study:

  • To evaluate aromatic C-H LSF.
  • To discuss current challenges and future directions in the field.
  • To provide insights into reactivity, chemoselectivity, site-selectivity, and substrate scope.

Main Methods:

  • Perspective-based evaluation of existing literature.
  • Analysis of aromatic C-H functionalization strategies.
  • Discussion of key criteria: reactivity, chemoselectivity, site-selectivity, and substrate scope.

Main Results:

  • Aromatic C-H LSF faces significant challenges in selectivity.
  • Current methods require careful consideration of substrate and reaction conditions.
  • Promising strategies are emerging for improved control.

Conclusions:

  • Aromatic C-H LSF is a rapidly developing field with significant potential.
  • Further research is needed to overcome selectivity challenges.
  • Future growth lies in developing more robust and versatile C-H functionalization methods.