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Related Concept Videos

Carbon Skeletons01:12

Carbon Skeletons

Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side chains...
Organic Compounds03:02

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Functional Groups02:45

Functional Groups

Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of that molecule. For example, the presence of certain functional groups on a molecule will make them hydrophilic, whereas others will make them hydrophobic. These functional groups are an indispensable part of organic chemistry and important components of biological molecules, such as carbohydrates, proteins, lipids, and nucleic acids. Each...
Functional Groups02:45

Functional Groups

Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of that molecule. For example, the presence of certain functional groups on a molecule will make them hydrophilic, whereas others will make them hydrophobic. These functional groups are an indispensable part of organic chemistry and important components of biological molecules, such as carbohydrates, proteins, lipids, and nucleic acids. Each...
Introduction to Functional Groups02:08

Introduction to Functional Groups


Functional groups are group of atoms with specific chemical properties that occur within organic molecules and sometimes denoted as “R”. Functional groups are found along the carbon backbone of macromolecules can form chains or rings of carbon atoms. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of common functional groups
The table below summarizes some of the major functional groups in organic chemistry. (The...
Functional Groups02:45

Functional Groups

Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of that molecule. For example, the presence of certain functional groups on a molecule will make them hydrophilic, whereas others will make them hydrophobic. These functional groups are an indispensable part of organic chemistry and important components of biological molecules, such as carbohydrates, proteins, lipids, and nucleic acids. Each...

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Related Experiment Video

Updated: Jul 10, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.

Jared H Delcamp1, M Christina White

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

Journal of the American Chemical Society
|November 23, 2006
PubMed
Summary

This study introduces a new palladium-catalyzed reaction for creating arylated allylic esters from simple olefins. This efficient method offers high selectivity and broad applicability in synthesizing complex molecules.

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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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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • C-H functionalization is a key strategy in modern organic synthesis.
  • Developing selective catalytic methods for C-H bond activation remains a significant challenge.
  • Palladium catalysis offers versatile pathways for C-H functionalization.

Purpose of the Study:

  • To develop a novel Pd(II)/sulfoxide-catalyzed method for sequential C-H oxidation and arylation.
  • To synthesize E-arylated allylic esters from alpha-olefins.
  • To establish a broadly applicable and efficient synthetic route for complex molecule fragments.

Main Methods:

  • Sequential allylic C-H oxidation followed by vinylic C-H arylation using a Pd(II)/sulfoxide catalyst system.
  • Utilizing alpha-olefins, carboxylic acids, and aryl boronic acids as starting materials.
  • Employing oxidative and acidic conditions at mild temperatures (room temperature to 45 °C).

Main Results:

  • Achieved high regio- and E:Z selectivities (>20:1) in the formation of E-arylated allylic esters.
  • Demonstrated broad substrate scope with respect to alpha-olefins, carboxylic acids, and aryl boronic acids.
  • Successfully synthesized densely functionalized fragments from abundant hydrocarbon starting materials.

Conclusions:

  • The developed Pd(II)/sulfoxide-catalyzed reaction provides an efficient and selective method for synthesizing E-arylated allylic esters.
  • This methodology enables the rapid assembly of complex molecular building blocks.
  • The reaction's broad scope and use of readily available starting materials highlight its potential for practical applications in organic synthesis.