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Related Concept Videos

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

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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.
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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.

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Related Experiment Video

Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Enone-alkyne reductive coupling: a versatile entry to substituted pyrroles.

Benjamin B Thompson1, John Montgomery

  • 1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.

Organic Letters
|June 11, 2011
PubMed
Summary

This study introduces a new synthetic route for creating diverse pyrrole structures. The method efficiently generates various substituted and fused pyrroles, overcoming limitations of existing approaches.

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

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Last Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Heterocyclic Chemistry

Background:

  • Pyrrole frameworks are crucial building blocks in medicinal chemistry and materials science.
  • Existing synthetic routes to substituted and polycyclic pyrroles often face limitations in scope and efficiency.
  • Access to 1,4-dicarbonyl intermediates is key for constructing pyrrole rings, but their preparation can be challenging.

Purpose of the Study:

  • To develop a versatile and efficient synthetic strategy for accessing a wide range of pyrrole derivatives.
  • To overcome the limitations associated with traditional methods for synthesizing 1,4-dicarbonyl compounds.
  • To demonstrate the broad applicability of the new method for constructing complex pyrrole architectures.

Main Methods:

  • Reductive coupling of enones or enals with alkynes.
  • Subsequent olefin oxidative cleavage of the coupled product.
  • Paal-Knorr cyclization to form the pyrrole ring.

Main Results:

  • The developed methodology provides a versatile entry to various pyrrole frameworks.
  • This approach successfully circumvents limitations of alternative synthetic routes to the required 1,4-dicarbonyl intermediate.
  • Accessible pyrrole classes include 2,3-, 2,4-, 1,2,3-, 1,2,4-, 2,3,5-, and 1,2,3,5-substituted monocyclic pyrroles.
  • The synthesis of fused-ring polycyclic pyrrole derivatives is also demonstrated.

Conclusions:

  • The combined sequence of reductive coupling, oxidative cleavage, and Paal-Knorr cyclization offers a powerful tool for pyrrole synthesis.
  • This strategy significantly expands the accessibility of diverse and complex pyrrole structures.
  • The method presents a valuable alternative for organic chemists seeking efficient routes to substituted and polycyclic pyrroles.