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Related Concept Videos

Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

5.0K
Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...
5.0K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

4.6K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
4.6K
Preparation of Nitriles01:12

Preparation of Nitriles

1.9K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
1.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

5.0K
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...
5.0K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.1K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
8.1K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.0K
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...
3.0K

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

Sunggi Lee1, Hyelee Lee, Kian L Tan

  • 1Boston College , 2609 Beacon Street Chestnut Hill, Massachusetts 02467.

Journal of the American Chemical Society
|December 12, 2013
PubMed
Summary
This summary is machine-generated.

Researchers developed a new nitrile-based template for meta-selective C-H bond functionalization. This versatile method is practical for various arenes and functional groups, simplifying synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Directed C-H functionalization is a powerful synthetic tool.
  • Meta-selective functionalization of arenes remains challenging.
  • Existing methods often lack broad substrate scope or functional group tolerance.

Purpose of the Study:

  • To develop a novel nitrile-based directing group for meta-selective C-H functionalization.
  • To demonstrate the broad applicability and functional group tolerance of the developed template.
  • To create a synthetically practical method for introducing and removing the directing group.

Main Methods:

  • Synthesis of a nitrile-based directing group featuring silicon attachment.
  • Application of the template in meta-selective C-H functionalization reactions.
  • Evaluation of substrate scope with various substituted arenes.
  • Assessment of functional group tolerance under reaction conditions.

Main Results:

  • A novel nitrile-based template enabling meta-selective C-H functionalization was successfully developed.
  • The template demonstrated applicability to a wide range of substituted arenes.
  • The method showed tolerance to diverse functional groups, enhancing its utility.
  • A facile introduction and deprotection strategy using a silicon linker was established.

Conclusions:

  • The developed nitrile-based template offers a practical and versatile approach for meta-selective C-H functionalization.
  • This methodology expands the synthetic toolkit for modifying aromatic compounds.
  • The silicon-mediated strategy enhances the overall efficiency and applicability in organic synthesis.