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Related Concept Videos

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

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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.
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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

12.0K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
12.0K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
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...
3.8K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.9K
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.
8.9K
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

6.1K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
6.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.3K
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.
2.3K

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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
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Recent Advancements in Nickel-Catalyzed Electrochemical Reductive Cross-Coupling.

Subban Kathiravan1, Ian A Nicholls1

  • 1Bioorganic & Biophysical Chemistry Laboratory, Linnaeus University Centre for Biomaterials Chemistry, Department of Chemistry & Biomedical Sciences, Linnaeus University, Kalmar SE-39182, Sweden.

ACS Organic & Inorganic Au
|December 8, 2025
PubMed
Summary

Nickel-catalyzed electrochemical cross-coupling offers a sustainable and precise approach to synthetic chemistry. Recent advancements focus on innovative catalysts and conditions for efficient, selective bond formation.

Keywords:
C−C, C−N, C−S, and C−P bond formationC−H activationelectrochemical synthesisnickel catalysisorganic electrochemistryreductive cross-couplingsustainable chemistrytransition-metal catalysis

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Area of Science:

  • Synthetic Chemistry
  • Electrochemistry
  • Catalysis

Background:

  • Nickel catalysis is versatile.
  • Electrochemical methods offer sustainability and precision.
  • Combining these offers significant advantages in synthesis.

Purpose of the Study:

  • To review recent progress in nickel-catalyzed electrochemical cross-coupling since 2015.
  • To highlight innovative catalysts, reaction conditions, and mechanistic insights.
  • To emphasize advancements in efficiency, selectivity, and sustainability.

Main Methods:

  • Literature review of developments from 2015 onwards.
  • Focus on novel nickel catalysts and reaction conditions.
  • Analysis of mechanistic insights into electrochemical synergy.

Main Results:

  • Development of innovative nickel catalysts.
  • Expansion of substrate scope for cross-coupling reactions.
  • Elucidation of mechanistic pathways benefiting from electrochemical methods.

Conclusions:

  • Nickel-catalyzed electrochemical cross-coupling is a rapidly advancing field.
  • This methodology facilitates complex bond formation under mild, sustainable conditions.
  • It holds significant potential for green and efficient synthetic chemistry.