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Related Concept Videos

Radical Formation: Elimination00:51

Radical Formation: Elimination

1.6K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
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Phase I Reactions: Reductive Reactions01:27

Phase I Reactions: Reductive Reactions

173
Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

9.9K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
9.9K
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction01:09

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

4.4K
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.                                       ...
4.4K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.6K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.6K
Elimination Reactions02:25

Elimination Reactions

13.2K
A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
13.2K

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Unlocking Catalysis Using Oxidatively Induced Reductive Elimination.

Carmen Antuña-Hörlein1, Jean-Pierre Djukic1

  • 1LCSOM, Institut de Chimie de Strasbourg, CNRS UMR 7177, Université de Strasbourg, 4 rue Blaise Pascal, 67000, Strasbourg, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 17, 2025
PubMed
Summary

Oxidatively induced reductive elimination (OIRE) is key for creating difficult products. This review explores OIRE

Keywords:
C−H bond activationOrganometallic catalysisOxidatively induced reductive eliminationTransition metals

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Oxidatively induced reductive elimination (OIRE) is vital for synthesizing complex molecules.
  • Historically studied in stoichiometric reactions, OIRE's catalytic applications are recent.
  • Ruthenium and Group 9 metals showcase OIRE modulation with various coupling partners.

Purpose of the Study:

  • To review the historical development and current state of OIRE chemistry.
  • To highlight key transition metals involved in OIRE and C-H bond functionalization.
  • To identify research gaps and the future potential of OIRE in catalysis.

Main Methods:

  • Literature review of historical and recent studies on OIRE.
  • Analysis of OIRE in stoichiometric and catalytic metal-centered reactions.
  • Exploration of OIRE's role in C-H bond functionalization.

Main Results:

  • OIRE is a powerful tool for accessing challenging chemical products.
  • Ruthenium, Group 9 metals (Rh, Ir), and 3d metals (Co) are significant in OIRE.
  • Metals like Ti, Mo, Fe, Hg, Ni, Ru, and Group 9 are key players in OIRE and C-H functionalization.

Conclusions:

  • OIRE is a crucial process in modern organometallic chemistry.
  • Further theoretical and mechanistic studies are needed to fully exploit OIRE.
  • Targeted application of OIRE in homogeneous catalysis holds significant promise.