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

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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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.
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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

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The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Alkylation-Terminated Catellani Reactions Using Alkyl Carbagermatranes.

Wei-Tao Jiang1, Meng-Yu Xu1, Shuo Yang1

  • 1Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.

Angewandte Chemie (International Ed. in English)
|July 22, 2020
PubMed
Summary
This summary is machine-generated.

This study introduces a new Catellani reaction method using alkyl carbagermatranes for efficient aromatic dialkylation. This breakthrough overcomes previous limitations, enabling reactions with β-H-containing compounds previously inaccessible.

Keywords:
Catellani reactioncarbagermatranesipso-alkylationmain-group chemistryorganogermanium compounds

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The Catellani reaction is a powerful tool for aromatic derivatization.
  • Previous Catellani reactions using alkyl electrophiles primarily achieved ortho-alkylation.
  • Ipso-alkylation-terminated Catellani reactions with β-H-containing reactants remained a challenge.

Purpose of the Study:

  • To develop a novel Catellani reaction for ipso-alkylation-terminated processes.
  • To explore the use of alkyl carbagermatranes (alkyl-Ge) as nucleophiles in the Catellani reaction.
  • To enable efficient dialkylation with β-H-containing reactants.

Main Methods:

  • Development of a new Catellani reaction protocol.
  • Utilizing alkyl carbagermatranes (alkyl-Ge) as nucleophiles.
  • Investigating the reactivity of alkyl-Ge and alkyl-boronic acids (alkyl-B(OH)2).

Main Results:

  • Successful alkylation-terminated Catellani reaction achieved.
  • Demonstrated efficient dialkylation using β-H-containing reactants.
  • Established the utility of alkyl-Ge as effective nucleophiles in this transformation.

Conclusions:

  • A novel Catellani reaction enabling ipso-alkylation-terminated dialkylation has been developed.
  • This method expands the scope of Catellani reactions to include previously inaccessible substrates.
  • Alkyl carbagermatranes offer a new avenue for nucleophilic participation in Catellani reactions.