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Related Concept Videos

Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.9K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.9K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.8K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

4.1K
The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
4.1K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.2K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.2K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

13.8K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
13.8K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

4.5K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
4.5K

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Related Experiment Video

Updated: Dec 29, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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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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N-Centered Radical Directed Remote C-H Bond Functionalization via Hydrogen Atom Transfer.

Gautam Kumar1, Suman Pradhan1, Indranil Chatterjee1

  • 1Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab, 140001, India.

Chemistry, an Asian Journal
|February 4, 2020
PubMed
Summary

N-centered radical directed remote C-H functionalization enables chemists to modify unactivated C-H bonds at distant sites. This powerful method is key for synthesizing complex heterocyclic scaffolds efficiently.

Keywords:
C−N/C−C bond formationN-centered radicalheterocycleshydrogen atom transferremote functionalization

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Last Updated: Dec 29, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Remote C-H bond functionalization is a growing area in organic synthesis.
  • N-centered radicals offer a pathway for directed remote C-H activation.

Purpose of the Study:

  • To explore N-centered radical directed remote C-H bond functionalization via hydrogen-atom-transfer.
  • To demonstrate the utility of this method for unactivated C-H bonds.

Main Methods:

  • Utilizing N-centered radicals to initiate hydrogen-atom-transfer reactions.
  • Targeting remote secondary, tertiary, and primary C-H bonds.

Main Results:

  • Successful functionalization of unactivated and remote C-H bonds.
  • Demonstrated applicability to diverse C-H bond types.

Conclusions:

  • N-centered radical directed remote C-H functionalization is a versatile synthetic tool.
  • This methodology facilitates the synthesis of valuable heterocyclic scaffolds.