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Related Concept Videos

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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

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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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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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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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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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Updated: Apr 11, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Photocatalytic Carbonyl Alkylative Amination via Direct C-H Functionalization.

Vaishnavi N Nair1, Madhu Sudan Manna1, Tiffany A Brisco1

  • 1Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.

Chem Catalysis
|April 10, 2026
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Summary

This study introduces a new photocatalytic method for synthesizing amines from aldehydes, anilines, and alkyl arenes. The efficient three-component coupling bypasses traditional steps, enabling diverse amine synthesis via C-H functionalization.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Amines are essential building blocks in numerous bioactive molecules.
  • Efficient and streamlined synthesis of amines from simple precursors is a significant challenge in organic chemistry.

Purpose of the Study:

  • To develop a novel photocatalytic three-component coupling reaction for amine synthesis.
  • To enable direct C-H functionalization of alkyl arenes for amine formation, avoiding preformed imines or organometallic reagents.

Main Methods:

  • Visible-light photocatalysis combined with Lewis acid catalysis.
  • Three-component coupling of aldehydes, anilines, and alkyl arenes.
  • Mechanistic studies and development of an enantioselective variant using a chiral copper catalyst.

Main Results:

  • Successful synthesis of diverse amines through a carbonyl alkylative amination pathway.
  • Demonstration of direct C-H functionalization of alkyl arenes.
  • Establishment of a broad scope reaction with high efficiency.
  • Development of an enantioselective method for asymmetric amine synthesis.

Conclusions:

  • The developed photocatalytic method offers a streamlined and efficient route to structurally diverse amines.
  • The reaction proceeds via direct C-H functionalization, showcasing a novel synthetic strategy.
  • The potential for asymmetric synthesis of amines has been demonstrated, expanding the utility of this methodology.