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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

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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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Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

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Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

5.5K
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...
5.5K
Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

4.6K
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...
4.6K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
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.
2.7K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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3.8K
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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The meta-Selective C-H Functionalization of Phenol Derivatives Using a Nitrile-Based Directing Group.

Kurella Mounika1, Dasari Srinivas1, Gedu Satyanarayana1

  • 1Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana 502284, India.

The Journal of Organic Chemistry
|June 3, 2025
PubMed
Summary
This summary is machine-generated.

This study presents a new method for meta-C-H olefination of phenols using a nitrile template. This approach achieves site-selective functionalization under mild conditions, overcoming previous limitations in regioselectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Ortho-C-H activation is well-established, but meta-C-H functionalization of phenols is difficult due to regioselectivity issues.
  • Traditional methods often require harsh conditions, limiting their applicability.
  • Developing selective and mild methods for meta-C-H functionalization is crucial for complex molecule synthesis.

Purpose of the Study:

  • To develop a site-selective meta-C-H olefination strategy for phenols.
  • To utilize an aliphatic nitrile as a directing template for regiocontrol.
  • To achieve this transformation under mild, room-temperature conditions.

Main Methods:

  • Employing an aliphatic nitrile as a directing group to guide metal-catalyzed C-H activation.
  • Leveraging nitrile-metal interactions for efficient and selective C-H bond cleavage.
  • Optimizing reaction conditions for mild, room-temperature operation.

Main Results:

  • Successful site-selective meta-C-H olefination of phenols was achieved.
  • The method demonstrated broad substrate scope and high efficiency.
  • The strategy was successfully applied to functionalize drug-like molecules and natural product derivatives with high yields and selectivity.

Conclusions:

  • A novel and efficient meta-C-H olefination strategy for phenols has been developed.
  • The nitrile-templated approach overcomes regioselectivity challenges under mild conditions.
  • This methodology offers a valuable tool for synthesizing complex organic molecules, including pharmaceuticals and natural products.