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Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

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

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

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 generating free carboxylic acid...

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis.

Mark S Chen1, M Christina White

  • 1Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, IL 61801, USA.

Science (New York, N.Y.)
|November 3, 2007
PubMed
Summary

A new iron catalyst enables selective oxidation of unactivated C-H bonds using hydrogen peroxide (H2O2). This breakthrough offers predictable control for complex molecule synthesis, streamlining organic chemistry.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Unactivated sp3 C-H bond oxidation is crucial for organic synthesis but requires highly reactive and selective catalysts.
  • Existing methods often lack predictable selectivity or require directing groups.

Purpose of the Study:

  • To develop a novel catalyst for efficient and selective oxidation of unactivated sp3 C-H bonds.
  • To demonstrate predictable selectivity based on substrate electronic and steric properties.
  • To explore the use of directing groups for specific product formation.

Main Methods:

  • Development of an iron (Fe)-based small molecule catalyst.
  • Utilizing hydrogen peroxide (H2O2) as the oxidant.
  • Testing catalyst reactivity and selectivity across a broad range of substrates, including complex natural products.

Main Results:

  • The Fe-based catalyst demonstrates high reactivity and predictable selectivity for C-H oxidation without directing groups.
  • Selectivity is governed by the electronic and steric nature of the C-H bonds.
  • Carboxylate directing groups enable the formation of five-membered ring lactones.
  • Complex natural products were modified at specific C-H bonds with preparatively useful yields.

Conclusions:

  • The developed catalyst provides a general and predictable method for aliphatic C-H oxidation.
  • This approach significantly streamlines the synthesis of complex molecules.
  • The catalyst expands the synthetic utility of C-H oxidation in organic chemistry.