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Related Concept Videos

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

4.4K
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...
4.4K
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

4.4K
Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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.
11.0K
Oxidation of Alcohols02:37

Oxidation of Alcohols

13.9K
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:
13.9K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.2K
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.
6.2K
Sharpless Epoxidation02:57

Sharpless Epoxidation

4.3K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
4.3K

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Light-driven Enzymatic Decarboxylation
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Light-driven Enzymatic Decarboxylation

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Highly efficient direct visible-light-mediated oxidative esterification of aldehydes.

Rickard Lindroth1, Hogan P Bryce-Rogers1, Thomas P M Merke1

  • 1Department of Chemistry and Molecular Biology, University of Gothenburg, Kemigården 4, 412 96, Gothenburg, Sweden.

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
|January 20, 2022
PubMed
Summary

Visible-light oxidation efficiently converts aldehydes to esters using indium triflate and N-bromosuccinimide (NBS). This one-pot method provides rapid access to diverse esters, including challenging tert-butyl esters.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Aldehyde oxidation is a fundamental transformation in organic synthesis.
  • Developing efficient and mild oxidation methods is crucial for sustainable chemistry.

Purpose of the Study:

  • To present a novel, efficient one-pot procedure for the direct oxidation of aldehydes to esters.
  • To utilize visible-light photocatalysis for ester synthesis.

Main Methods:

  • Employed a catalytic system of indium triflate and N-bromosuccinimide (NBS).
  • Utilized visible-light irradiation as the energy source.
  • Tested the reaction with various aldehydes and ortho-esters or alcohols.

Main Results:

  • Achieved direct oxidation of aldehydes to esters in a one-pot procedure.
  • Demonstrated rapid conversion for many substrates, some within seconds.
  • Obtained good yields for challenging tert-butyl esters within 4 hours.

Conclusions:

  • The developed method offers an efficient and rapid route to various esters.
  • Visible-light-mediated oxidation presents a sustainable alternative for ester synthesis.
  • The protocol is effective for both simple and sterically hindered substrates.