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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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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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Halogenation of Alkenes02:46

Halogenation of Alkenes

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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.
18.2K
Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

4.6K
Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Lactonization as a general route to β-C(sp3)-H functionalization.

Zhe Zhuang1, Jin-Quan Yu2

  • 1Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA.

Nature
|December 12, 2019
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Summary

This study introduces a new palladium-catalyzed method for functionalizing aliphatic acids at the beta position. This efficient beta-C-H lactonization enables selective modifications, offering a scalable route to valuable carboxylic acid derivatives.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Beta-C-H functionalization of aliphatic acids is a key synthetic strategy but faces limitations like poor selectivity and expensive reagents.
  • Existing methods often require directing groups and are not suitable for free aliphatic acids or industrial scales.

Purpose of the Study:

  • To develop a novel, efficient, and scalable method for beta-C(sp3)-H functionalization of aliphatic acids.
  • To overcome the limitations of existing beta-C-H activation reactions, particularly for industrial applications.

Main Methods:

  • A palladium-catalyzed beta-C(sp3)-H lactonization reaction was developed.
  • A mono-N-protected beta-amino acid ligand was employed to enable the catalytic cycle.
  • Tert-butyl hydrogen peroxide was used as an inexpensive oxidant.

Main Results:

  • The reaction successfully achieved mono-selective beta-C(sp3)-H lactonization of aliphatic acids.
  • The generated beta-lactone intermediates allowed for the installation of diverse functional groups (alkyl, alkenyl, aryl, alkynyl, fluoro, hydroxyl, amino) at the beta position.
  • The process demonstrated ease of product purification without column chromatography.

Conclusions:

  • This Pd-catalyzed lactonization provides a versatile and scalable route to functionalized carboxylic acids.
  • The method's compatibility with free acids, use of inexpensive reagents, and amenability to large-scale manufacturing make it industrially relevant.