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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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.
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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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.
10.8K
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
3.2K
Oxidation of Alcohols02:37

Oxidation of Alcohols

13.4K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Light-driven Enzymatic Decarboxylation
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Light-driven Enzymatic Decarboxylation

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Decarboxylative oxidation-enabled consecutive C-C bond cleavage.

Ruining Li1, Ya Dong1, Shah Nawaz Khan1

  • 1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Pharm-X Center, School of Pharmacy, Shanghai Jiao Tong University, No. 800 Dongchuan Rd., Shanghai, 200240, China.

Nature Communications
|November 18, 2022
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for selective carbon-carbon bond cleavage using photoredox and copper catalysis. This approach enables the scission of inert bonds in carboxylic acids, offering novel synthetic possibilities.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Selective carbon-carbon (C-C) bond cleavage is crucial for chemical synthesis, offering an alternative to traditional methods focused on molecular construction.
  • Existing C-C cleavage techniques, particularly for C(sp³)-C(sp³) bonds, have limitations, often requiring strained rings or specific radical precursors.

Purpose of the Study:

  • To develop a novel method for the selective cleavage of inert C(sp³)-C(sp³) bonds.
  • To utilize α-trisubstituted carboxylic acids as substrates for C-C bond scission.

Main Methods:

  • Integration of photoredox catalysis with copper catalysis.
  • Employing a decarboxylative oxidation process to generate alkoxy radicals in situ.
  • Achieving consecutive C-C bond cleavage, including the scission of a β-CH₂ group.

Main Results:

  • Demonstrated the selective cleavage of inert β-CH₂ groups within α-trisubstituted carboxylic acids.
  • Successfully merged photoredox and copper catalysis to achieve this transformation.
  • The decarboxylative oxidation initiated a cascade of C-C bond cleavage events.

Conclusions:

  • The developed method provides a new pathway for cleaving robust C(sp³)-C(sp³) bonds.
  • This approach expands the toolkit for synthetic chemists seeking to break down molecular complexity.
  • The findings may inspire further research into novel C-C bond activation strategies.