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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Developments in fluorocyclization methodologies.

Susan C Wilkinson1, Roger Salmon, Véronique Gouverneur

  • 1The Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OXI 3TA, UK.

Future Medicinal Chemistry
|March 24, 2011
PubMed
Summary
This summary is machine-generated.

Developing novel asymmetric fluorocyclization methods is crucial for creating complex fluorinated heterocycles. These advanced building blocks are essential for medicinal chemistry and drug discovery, enabling precise stereochemical control.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor
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Last Updated: Jun 3, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor
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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Fluorine Chemistry

Background:

  • Fluorinated organic compounds are prevalent in marketed drugs.
  • Heterocycles are common motifs in lead compounds, making fluorinated heterocycles valuable building blocks.
  • Fluorocyclization reactions are key for synthesizing complex fluoro-heterocycles.

Purpose of the Study:

  • To highlight the importance of fluorocyclization reactions in synthesizing fluorinated heterocycles.
  • To identify the limitations in current asymmetric fluorocyclization methodologies.
  • To emphasize the need for conceptual advances in asymmetric fluoroheterocyclization for medicinal chemistry.

Main Methods:

  • Review of existing fluorocyclization strategies, including those with nucleophilic and electrophilic fluorine sources.
  • Analysis of mechanistic pathways (fluorination before or after cyclization).
  • Examination of diastereoselectivity in fluorocyclization reactions.

Main Results:

  • Fluorocyclization protocols have been used to synthesize rare fluorinated biologically active molecules.
  • Optimal diastereocontrol is achieved when cyclization precedes fluorination.
  • Asymmetric fluorocyclizations are largely unexplored, with limited examples like the Nazarov fluorination process.

Conclusions:

  • Asymmetric fluoroheterocyclizations remain an underexplored area.
  • Significant conceptual advancements are required to develop methods for programmable stereocontrol in fluoroheterocycle synthesis.
  • Such advancements are essential for the application of these building blocks in medicinal chemistry.