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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

15.2K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
15.2K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.5K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
3.5K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.3K
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...
5.3K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.2K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.7K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
12.7K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

4.9K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
4.9K

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Updated: May 24, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

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Asymmetric Counteranion-Directed Halogen Bonding Catalysis.

Dominik L Reinhard1,2, Anna Iniutina2, Sven Reese1

  • 1Fakultät für Chemie und Biochemie, Organische Chemie II, Ruhr-Universität Bochum, 44801 Bochum, Germany.

Journal of the American Chemical Society
|March 3, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a novel asymmetric catalysis method combining halogen bonding and counteranion-directed catalysis. This approach achieves highly enantioselective synthesis for key pharmaceutical intermediates.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Halogen bonding is a recognized tool in organocatalysis.
  • Asymmetric halogen bonding applications are limited, with few studies using chiral halogen bond donors.

Purpose of the Study:

  • To develop the first highly enantioselective method combining halogen bonding with asymmetric counteranion-directed catalysis.
  • To apply this method to the asymmetric organocatalysis of a Diels-Alder reaction.

Main Methods:

  • Utilized a strong bidentate iodine(III)-based catalyst.
  • Employed chiral disulfonimides as counteranions for asymmetric induction.
  • Investigated the Diels-Alder reaction between cyclopentadiene and trans-β-nitrostyrene.

Main Results:

  • Achieved the first highly enantioselective organocatalytic Diels-Alder reaction using this combined approach.
  • Successfully synthesized fencamfamine precursor with high enantioselectivity.
  • Demonstrated the efficacy of the chiral iodine(III) catalyst and disulfonimide counteranions.

Conclusions:

  • The combination of halogen bonding and asymmetric counteranion-directed catalysis is a powerful strategy for enantioselective organocatalysis.
  • This method provides a new route for the asymmetric synthesis of valuable pharmaceutical compounds.
  • Highlights the potential of chiral iodine(III) catalysts in asymmetric synthesis.