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Related Concept Videos

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

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...
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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Related Experiment Video

Updated: Jun 29, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Catalytic intermolecular allylic C-H alkylation.

Andrew J Young1, M Christina White

  • 1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.

Journal of the American Chemical Society
|October 4, 2008
PubMed
Summary

This study introduces the first electrophilic palladium-catalyzed allylic C-H alkylation, enabling direct sp3-sp3 carbon-carbon bond formation. This novel method efficiently synthesizes valuable nitro-arylpentenoates from simple starting materials.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-carbon bond formation is fundamental in organic synthesis.
  • Direct functionalization of C-H bonds offers atom economy and step efficiency.
  • Allylic C-H functionalization remains a challenging area in catalysis.

Purpose of the Study:

  • To develop a novel electrophilic palladium-catalyzed method for allylic C-H alkylation.
  • To establish a direct route for sp3-sp3 C-C bond formation from C-H bonds.
  • To synthesize valuable intermediates for further chemical transformations.

Main Methods:

  • Electrophilic Pd(II)-catalyzed reaction.
  • Utilized terminal olefin substrates and methyl nitroacetate.
  • Employed dimethyl sulfoxide (DMSO) as a crucial pi-acidic ligand.

Main Results:

  • Achieved the first reported electrophilic Pd(II)-catalyzed allylic C-H alkylation.
  • Synthesized a diverse range of aromatic and heteroaromatic linear (E)-alpha-nitro-arylpentenoates.
  • Obtained products as single olefin isomers in excellent yields.

Conclusions:

  • The developed method provides a novel and efficient pathway for C-C bond formation.
  • The synthesized nitro-arylpentenoates are versatile intermediates.
  • Products can be readily converted to amino esters and amino acid precursors.