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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

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Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
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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...
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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.
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Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
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Electrolysis-Assisted Reduction of Dimethylformamide for Unactivated Alkene Functionalizations.

Yifan Xi1, Sulekha Sharma1, C Oliver Kappe1,2

  • 1Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz, Austria.

Journal of the American Chemical Society
|March 2, 2026
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Researchers developed a new method to activate N,N-Dimethylformamide, a common solvent, using electrolysis. This technique enables the functionalization of alkenes, creating valuable hydroformylated and hydroaminomethylated products through radical intermediates.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • N,N-Dimethylformamide (DMF) is a versatile solvent and reagent.
  • Direct single-electron reduction of DMF is challenging due to its low reductive potential.
  • Novel activation strategies for DMF are needed for broader synthetic applications.

Purpose of the Study:

  • To present a novel electrolysis-assisted method for generating the N,N-dimethylformamide distonic radical anion.
  • To demonstrate the synthetic utility of this radical intermediate in functionalizing unactivated alkenes.
  • To explore new radical transformations involving DMF.

Main Methods:

  • Electrolysis-assisted generation of the N,N-dimethylformamide distonic radical anion.
  • Application of the radical anion in the functionalization of various mono- and disubstituted alkenes.
  • Mechanistic studies using electrochemical methods and product analysis.

Main Results:

  • Successful generation of the N,N-dimethylformamide distonic radical anion at a magnesium anode.
  • Demonstrated synthetic applicability through hydroformylation and hydroaminomethylation of unactivated alkenes.
  • Validated the transformation across a range of olefin substrates.

Conclusions:

  • Electrolysis provides an effective route to activate N,N-Dimethylformamide via its radical anion.
  • This method offers a new pathway for alkene functionalization, yielding valuable products.
  • The findings open avenues for further radical-based transformations utilizing DMF.