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Related Concept Videos

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

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Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
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α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

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

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.7K
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...
3.7K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

17.9K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.1K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
10.1K
Alkyl Halides02:45

Alkyl Halides

16.5K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.

Takashi Nishikata1

  • 1Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan.

Chemistryopen
|July 11, 2024
PubMed
Summary

α-Bromocarbonyl compounds with tertiary carbons are versatile reagents in organic synthesis. Recent advances have expanded their use beyond radical initiation to nucleophilic, electrophilic, and organometallic reactions, enabling complex molecular construction.

Keywords:
additionasymmetric reactioncross-couplingtertiary alkyl radicaltertiary alkylation

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Area of Science:

  • Synthetic Organic Chemistry
  • Radical Chemistry
  • Organometallic Chemistry

Background:

  • α-Bromocarbonyl compounds with tertiary carbons were historically limited to radical initiator roles in atom transfer radical polymerization (ATRP).
  • The advent of photo-radical reactions around 2010 spurred interest in these compounds as tertiary alkyl radical precursors.
  • Emerging research revealed broader reactivity beyond radical chemistry.

Purpose of the Study:

  • To review the diverse synthetic organic chemical value of α-bromocarbonyl compounds featuring tertiary carbons.
  • To highlight their expanded applications in various reaction types beyond radical initiation.
  • To showcase their utility in modern organic synthesis and total synthesis strategies.

Main Methods:

  • Comprehensive literature survey of α-bromocarbonyl compound reactivity up to 2022.
  • Analysis of their roles as radical precursors, nucleophiles, electrophiles, and in organometallic/ionic reactions.
  • Examination of their application in diverse synthetic transformations including multi-component reactions, cross-coupling, and cyclizations.

Main Results:

  • α-Bromocarbonyl compounds with tertiary carbons exhibit dual nucleophilic and electrophilic character.
  • They serve as versatile precursors for tertiary alkylation, a previously challenging transformation.
  • Their application spans a wide array of organic reactions, including stereospecific and asymmetric synthesis.

Conclusions:

  • α-Bromocarbonyl compounds are indispensable tools in contemporary organic synthesis, offering broad reactivity.
  • Their unique properties facilitate complex molecular assembly and total synthesis.
  • These compounds have significantly advanced the field of tertiary alkylation, opening new synthetic avenues.