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Related Concept Videos

Carbocations02:10

Carbocations

10.8K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

5.0K
The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the...
5.0K
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

4.0K
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
4.0K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

3.2K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
3.2K
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

3.8K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
3.8K
Conjugate Addition of Enolates: Michael Addition01:08

Conjugate Addition of Enolates: Michael Addition

2.4K
The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
2.4K

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Single-Electron-Transfer-Mediated Carbonylation Reactions.

Le-Cheng Wang1,2, Xiao-Feng Wu1,2

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|March 5, 2025
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Single-electron-transfer (SET)-mediated carbonylation offers a sustainable alternative to traditional methods, enabling efficient synthesis of valuable carbonylated products from bulk chemicals like alkanes and alkyl halides. This approach utilizes milder conditions and reduces reliance on precious metals, enhancing scalability and applications in drug discovery.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Transition-metal-catalyzed carbonylation is crucial for producing carbonylated products but faces challenges like precious metal dependence and harsh conditions.
  • Single-electron-transfer (SET)-mediated carbonylation presents a promising alternative, enabling transformations of previously unreactive substrates.
  • Developing efficient carbonylation methods using abundant bulk chemicals is essential for industrial scalability and sustainability.

Purpose of the Study:

  • To develop novel SET-mediated carbonylation reactions utilizing bulk chemicals such as alkanes and alkyl halides.
  • To explore two key strategies: single-electron reduction of C(sp3)-X bonds and single-electron oxidation of C(sp3)-H bonds.
  • To expand the scope of carbonylation reactions, including radical relay processes for alkenes and applications in drug discovery.

Main Methods:

  • Activation of C(sp3)-X bonds via single-electron reduction, overcoming challenges associated with highly negative reduction potentials.
  • Activation of C(sp3)-H bonds via single-electron oxidation using 3d metal catalysts, promoting efficiency and atom utilization.
  • Facilitation of radical relay carbonylation of alkenes using transition metal or photoredox catalysis for controlled reaction pathways.

Main Results:

  • Successful development of SET-mediated carbonylation of alkanes and alkyl halides, yielding high-value carbonylated products.
  • Demonstration of efficient aminocarbonylation and alkoxycarbonylation of diverse C(sp3)-H bonds.
  • Achieved various alkene transformations including oxyalkylative, aminoalkylative, and fluoroalkylative carbonylation with high selectivity.

Conclusions:

  • SET-mediated carbonylation significantly enhances the sustainability and scalability of carbonylation processes.
  • The developed methods provide precise control over reaction intermediates, leading to high selectivity for diverse carbonylated products.
  • These versatile carbonylation strategies are valuable for late-stage functionalization in drug discovery and medicinal chemistry.