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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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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...
10.4K
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

3.4K
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]...
3.4K
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction01:09

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

4.5K
Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.                                       ...
4.5K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
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...
3.3K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
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.
7.7K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.4K
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.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.4K

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Related Experiment Video

Updated: Jun 29, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

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NAD(P)H-Inspired CO2 Reduction Based on Organohydrides.

Wenjin Dong1, Chuanjun Wang1, Yutai Zou1,2

  • 1Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Shandong Energy Institute, Qingdao New Energy Shandong Laboratory, Qingdao 266101, China.

ACS Applied Materials & Interfaces
|March 29, 2024
PubMed
Summary

Metal-free catalysts offer a sustainable solution for converting carbon dioxide (CO2) into valuable products. Organohydrides, inspired by natural photosynthesis, show significant promise as efficient and eco-friendly alternatives for CO2 reduction (CO2R).

Keywords:
CO2 reductionNAD(P)Hcatalystscofactor mimicsmetal-freeorganohydrides

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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
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Area of Science:

  • Green Chemistry
  • Catalysis
  • Sustainable Energy

Background:

  • Global environmental crisis driven by CO2 emissions.
  • Need for cost-effective, eco-friendly CO2 conversion technologies.
  • Natural photosynthesis utilizes NADPH for CO2 reduction.

Purpose of the Study:

  • Review metal-free catalysts for CO2 conversion.
  • Highlight NAD(P)H-inspired organohydrides for CO2 reduction (CO2R).
  • Discuss advancements and potential of organohydrides as sustainable catalysts.

Main Methods:

  • Summarize photosensitizers for NAD(P)H regeneration.
  • Introduce NAD(P)H-inspired organohydrides and their redox applications.
  • Analyze recent breakthroughs in organohydride-catalyzed CO2R.

Main Results:

  • Organohydrides demonstrate remarkable potential for efficient metal-free CO2R.
  • These compounds offer tunable reducibility, mimicking natural systems.
  • Organohydrides show promise as sustainable alternatives to metal catalysts.

Conclusions:

  • Organohydride catalysts are a promising avenue for CO2 valorization.
  • Further research can advance organohydride-based CO2R technologies.
  • These catalysts contribute to mitigating the global environmental crisis.