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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.6K
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.
9.6K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

4.1K
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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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

4.4K
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...
4.4K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

3.4K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Cobalt(III)-Catalyzed Directed C-H Allylation.

Tobias Gensch1, Suhelen Vásquez-Céspedes1, Da-Gang Yu1

  • 1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.

Organic Letters
|July 15, 2015
PubMed
Summary

Cobalt(III) catalysis enables amide-directed C-H activation for allylation of arenes, heteroarenes, and olefins. This method efficiently introduces allyl groups using various allyl sources.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • C-H activation is a crucial strategy in modern organic synthesis.
  • Developing efficient catalytic systems for C-H functionalization remains a significant challenge.
  • Amide-directed C-H activation offers regioselective control for functionalizing specific positions in organic molecules.

Purpose of the Study:

  • To develop a novel cobalt(III)-catalyzed method for the allylation of C-H bonds.
  • To explore the scope and limitations of this new catalytic system.
  • To demonstrate the utility of the developed method for synthesizing allylated compounds.

Main Methods:

  • Cobalt(III) catalysis was employed to achieve amide-directed C-H activation.
  • A range of arenes, heteroarenes, and olefins were subjected to allylation.
  • Various allyl sources were investigated to optimize the introduction of the allyl group.

Main Results:

  • The developed cobalt(III)-catalyzed reaction successfully achieved allylation via C-H activation.
  • The methodology proved effective for a diverse set of substrates, including arenes, heteroarenes, and olefins.
  • The use of readily available allyl sources facilitated the introduction of the allyl functional group.

Conclusions:

  • A new and efficient cobalt(III)-catalyzed allylation of C-H bonds has been established.
  • This method provides a versatile route for the synthesis of allylated compounds through directed C-H activation.
  • The developed protocol offers a valuable tool for organic chemists seeking to incorporate allyl groups into complex molecules.