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

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

6.3K
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...
6.3K
Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

4.9K
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...
4.9K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
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.
2.9K
Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

6.9K
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...
6.9K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.7K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
5.7K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.8K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.8K

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Transformable/modifiable directing group-assisted C(sp2)-H functionalizations.

Bubul Das1,2, Nikita Chakraborty1, Bhisma K Patel1

  • 1Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India. patel@iitg.ac.in.

Organic & Biomolecular Chemistry
|August 26, 2025
PubMed
Summary
This summary is machine-generated.

This review explores transformable directing groups for metal-catalyzed C-H functionalization. These groups simplify synthesis by avoiding extra removal steps, enabling efficient one-pot reactions.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Directing groups are crucial for regioselective C-H functionalization using transition metals.
  • Current methods often require additional steps for directing group removal, increasing synthetic complexity.

Purpose of the Study:

  • To review recent advancements in transformable/modifiable directing groups for C-H functionalization.
  • To highlight their role in one-pot and step-economical synthesis of complex organic scaffolds.

Main Methods:

  • Discussion of literature on transition metal-catalyzed C-H activation.
  • Focus on directing groups that can be transformed or modified post-functionalization.
  • Analysis of one-pot and step-economical synthetic strategies.

Main Results:

  • Transformable directing groups offer a solution to the limitation of post-functionalization removal.
  • These groups can be converted into other functionalities in one pot or modified easily.
  • Enables the synthesis of complex organic structures with improved efficiency.

Conclusions:

  • Transformable directing groups significantly enhance the utility of C-H functionalization.
  • They streamline synthetic routes, reducing step count and waste.
  • Facilitate the construction of intricate molecular architectures.