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Related Concept Videos

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

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

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

Directing Effect of Substituents: meta-Directing Groups

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

Directing Effect of Substituents: ortho–para-Directing Groups

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 electrons...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

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 the...
Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

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...

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Removable directing groups in organic synthesis and catalysis.

Géraldine Rousseau1, Bernhard Breit

  • 1Institut für Organische Chemie und Biochemie, Freiburg Institute for Advanced Studies (FRIAS), Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg i. Brsg., Germany.

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Directing groups offer precise control in transition-metal catalysis and organometallic reactions. Removable directing groups enable challenging transformations when inherent functional groups are unsuitable.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Directing groups are crucial for controlling selectivity in transition-metal catalysis.
  • Existing functional groups may not always facilitate efficient intramolecular delivery of catalysts or reagents.

Purpose of the Study:

  • To provide a comprehensive overview of the state-of-the-art in directing group chemistry.
  • To highlight the application of removable directing groups for overcoming limitations in substrate functionalization.

Main Methods:

  • Review of literature on directing group strategies.
  • Analysis of stoichiometric and catalytic applications of directing groups.

Main Results:

  • Directing groups enable fine-tuned control over reaction selectivity.
  • Removable directing groups offer a versatile solution for challenging synthetic targets.
  • Overview covers both stoichiometric and catalytic uses.

Conclusions:

  • Directing groups are indispensable tools in modern synthetic chemistry.
  • The development and application of removable directing groups significantly expand synthetic possibilities.
  • This review synthesizes current knowledge on directing group utility.