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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

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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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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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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.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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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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Oxidative Alkane C-H Alkoxycarbonylation.

Lijun Lu1, Renyi Shi1, Luyao Liu1

  • 1College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, Wuhan, 430072, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 17, 2016
PubMed
Summary

This study introduces a new palladium-catalyzed method for alkane carbonylation, efficiently synthesizing alkyl carboxylates from abundant feedstocks like ethane. This advances direct functionalization of unactivated C-H bonds using carbon monoxide.

Keywords:
C−H activationalkanescarbonylationpalladiumradical reactions

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Synthesis

Background:

  • Directly converting chemical feedstocks into valuable compounds is a key goal in organic synthesis.
  • Oxidative carbonylation of alkanes via C(sp(3))-H activation offers an efficient route to carbonyl derivatives.
  • The low reactivity of unactivated alkanes (high C-H bond dissociation energy, low polarity) presents a significant challenge for carbonylation.

Purpose of the Study:

  • To develop a novel method for the oxidative alkoxycarbonylation of unactivated alkanes.
  • To enable the synthesis of diverse alkyl carboxylates from readily available feedstocks, including natural gas components.

Main Methods:

  • A palladium-catalyzed radical oxidative alkoxycarbonylation reaction was developed.
  • The method utilizes alkanes and carbon monoxide (CO) gas in the presence of various alcohols.
  • Reaction conditions were optimized for efficiency and substrate scope.

Main Results:

  • The developed method successfully synthesized numerous alkyl carboxylates from various alkanes and alcohols.
  • Product yields reached up to 94% under optimized conditions.
  • Ethane, a primary component of natural gas, was effectively utilized as a substrate, demonstrating the method's potential for utilizing abundant resources.

Conclusions:

  • A novel and efficient palladium-catalyzed radical oxidative alkoxycarbonylation of alkanes has been established.
  • This method overcomes the challenge of functionalizing unactivated C(sp(3))-H bonds.
  • The compatibility with diverse substrates, including ethane, highlights its significance for sustainable synthesis and feedstock utilization.