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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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

Directing Effect of Substituents: ortho–para-Directing Groups

6.4K
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...
6.4K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

4.5K
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...
4.5K
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
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.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Arene C-H functionalisation using a removable/modifiable or a traceless directing group strategy.

Fengzhi Zhang1, David R Spring

  • 1College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, P. R. China 310014. fz233@cam.ac.uk.

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Summary

Removable directing groups enable versatile aromatic C-H functionalization. This strategy overcomes limitations of traditional directing groups, expanding synthetic possibilities for diverse molecular structures.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Coordinating moieties are effective directing groups for aromatic carbon-hydrogen (C-H) bond functionalization.
  • This enables selective carbon-carbon (C-C) and carbon-heteroatom (C-X) bond formation in arenes.
  • A key limitation is the difficulty in removing or modifying many directing groups post-functionalization, restricting product diversity.

Purpose of the Study:

  • To review recent advances in the use of removable, modifiable, or traceless directing groups for C-H functionalization.
  • To highlight how these groups overcome limitations of traditional directing groups.
  • To demonstrate the increased synthetic applicability of C-H functionalization processes.

Main Methods:

  • Overview of literature on directing group strategies for C-H functionalization.
  • Focus on directing groups that can be easily attached and detached from substrates.
  • Discussion of synthetic applications enabled by these advanced directing groups.

Main Results:

  • Removable/modifiable/traceless directing groups significantly enhance the utility of C-H functionalization.
  • These strategies allow for greater structural diversity in the final products.
  • The field has seen dramatic increases in synthetic applicability due to these advancements.

Conclusions:

  • Employing removable or traceless directing groups is crucial for expanding the scope of arene C-H functionalization.
  • This approach provides a powerful toolkit for chemists to access a wider range of complex molecules.
  • The development of such directing groups is transforming synthetic organic chemistry.