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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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.
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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Properties of Organometallic Compounds

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Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
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Handling fluorinated gases as solid reagents using metal-organic frameworks.

Kaitlyn T Keasler1, Mary E Zick1, Emily E Stacy1

  • 1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14850, USA.

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|September 28, 2023
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Summary
This summary is machine-generated.

Researchers developed a safer way to use fluorinated gases in drug discovery by storing them in solid metal-organic frameworks (MOFs). This innovation simplifies late-stage fluorination reactions, making them more accessible for pharmaceutical and agrochemical development.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Chemical Engineering

Background:

  • Fluorine incorporation enhances drug bioavailability and metabolic stability.
  • Fluorinated gases are valuable for late-stage fluorination but difficult to handle.
  • Specialized equipment is typically required for using gaseous fluorinating agents.

Purpose of the Study:

  • To develop a safe and accessible method for utilizing fluorinated gases in organic synthesis.
  • To create benchtop-stable solid reagents from volatile fluorinated gases.
  • To enable late-stage fluorovinylation and fluoroalkylation reactions without specialized equipment.

Main Methods:

  • Utilizing metal-organic frameworks (MOFs) to encapsulate fluorinated gases.
  • Preparing gram-scale quantities of gas-MOF reagents.
  • Encapsulating gas-MOF reagents in wax for stable storage and controlled release via sonication.
  • Applying these reagents in fluorovinylation and fluoroalkylation reactions.

Main Results:

  • Demonstrated the preparation of gram-scale gas-MOF reagents.
  • Successfully used gas-MOF reagents for fluorovinylation and fluoroalkylation.
  • Showcased wax encapsulation for benchtop stability and controlled gas release.
  • Established a safer alternative to direct handling of fluorinated gases.
  • Enabled high-throughput reaction development using these novel reagents.

Conclusions:

  • Metal-organic frameworks provide a versatile platform for transforming hazardous fluorinated gases into user-friendly solid reagents.
  • This approach significantly improves the safety and accessibility of late-stage fluorination in pharmaceutical and agrochemical research.
  • The developed method facilitates efficient and high-throughput synthesis, accelerating the discovery of novel fluorinated compounds.