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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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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...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

3.1K
A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
3.1K
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

4.3K
Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
4.3K
Halogenation of Alkenes02:46

Halogenation of Alkenes

20.8K
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.
20.8K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

15.0K
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.
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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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Dearomatization through Halofunctionalization Reactions.

Xiao-Wei Liang1, Chao Zheng1, Shu-Li You2

  • 1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 6, 2016
PubMed
Summary
This summary is machine-generated.

This review covers dearomatization via halofunctionalization, detailing strategies like electrophilic halogenation of alkynes/alkenes and direct arene halogenation. These methods yield valuable halogenated polycyclic compounds.

Keywords:
arenesasymmetric catalysisdearomatizationhalogenationsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Dearomatization reactions are crucial for synthesizing complex molecules.
  • Halofunctionalization offers a pathway to introduce halogens and create new molecular frameworks.

Purpose of the Study:

  • To summarize recent advancements in dearomatization via halofunctionalization reactions.
  • To categorize and explain the primary strategies employed in this field.
  • To highlight the synthesis of valuable halogenated polycyclic architectures.

Main Methods:

  • Electrophilic halogenation of alkyne or alkene moieties followed by ipso-cyclization.
  • Direct electrophilic halogenation of substituted arenes, followed by deprotonation or nucleophilic trapping.
  • Enantioselective variants utilizing organocatalysis or transition metal catalysis.

Main Results:

  • Two main strategies for dearomatization via halofunctionalization have been identified.
  • Valuable halogenated polycyclic molecular architectures can be synthesized from accessible starting materials.
  • Highly enantioselective methods have been developed for certain dearomatization pathways.

Conclusions:

  • Dearomatization through halofunctionalization is a versatile synthetic tool.
  • The reviewed methods enable the construction of complex halogenated molecules.
  • Continued development in this area promises access to novel chemical structures.