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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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Phase I Reactions: Reductive Reactions01:27

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Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
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Reactions at the Benzylic Position: Oxidation and Reduction00:59

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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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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.
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Reactivity in Nickel-Catalyzed Multi-component Sequential Reductive Cross-Coupling Reactions.

Haifeng Chen1, Huifeng Yue1, Chen Zhu1

  • 1KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.

Angewandte Chemie (International Ed. in English)
|June 21, 2022
PubMed
Summary
This summary is machine-generated.

A new nickel-catalyzed reaction efficiently synthesizes aryl-alkyl ketones using ethyl chloroformate as a safe carbon monoxide source. This three-component reductive carbonylation offers a practical method with broad applicability.

Keywords:
Alkyl HalidesAryl HalidesCarbonylationEthyl ChloroformateNickel

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbonylation reactions are crucial for synthesizing carbonyl compounds.
  • Traditional methods often require toxic or hazardous carbon monoxide sources.
  • Developing safer and more efficient carbonylation protocols is an ongoing challenge.

Purpose of the Study:

  • To develop a novel nickel-catalyzed three-component reductive carbonylation protocol.
  • To utilize ethyl chloroformate as a convenient and safe carbon monoxide surrogate.
  • To synthesize aryl-alkyl ketones efficiently.

Main Methods:

  • Nickel-catalyzed three-component reaction involving alkyl halides, aryl halides, and ethyl chloroformate.
  • Optimization of reaction conditions.
  • Experimental and Density Functional Theory (DFT) mechanistic studies.

Main Results:

  • Successful synthesis of aryl-alkyl ketones via reductive carbonylation.
  • Ethyl chloroformate effectively served as a CO source.
  • The reaction demonstrated a wide substrate scope and good functional group tolerance.
  • Mechanistic studies elucidated the complex cross-electrophile coupling and oxidative addition sequence.

Conclusions:

  • The developed protocol provides an efficient and practical method for aryl-alkyl ketone synthesis.
  • Ethyl chloroformate is a viable and safe alternative to gaseous CO.
  • The study offers insights into the intricate mechanism of nickel-catalyzed cross-electrophile coupling.