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Related Concept Videos

Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

928
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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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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Introduction to Functional Groups02:08

Introduction to Functional Groups

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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...
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
3.5K
Overview of Advanced Functional Groups02:22

Overview of Advanced Functional Groups

23.3K

Functional groups are groups of atoms with specific chemical properties that occur within organic molecules and are sometimes denoted as “R”. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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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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Cryogenic Organometallic Carbon-Fluoride Bond Functionalization with Broad Functional Group Tolerance.

D Lucas Kane1, Bryan C Figula1, Kaluvu Balaraman1

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|February 6, 2025
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This study introduces a novel method for functionalizing the robust carbon-fluorine (C-F) bond under mild cryogenic conditions. This breakthrough enables selective carbon-carbon bond formation using alkyl fluorides, previously challenging due to the C-F bond

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • Fluorinated organic compounds possess unique properties valuable in chemical and pharmaceutical sciences.
  • The high stability of the carbon-fluorine (C-F) bond limits its synthetic utility compared to other alkyl halides.
  • Existing methods for C-F bond functionalization are often limited in scope or require harsh conditions.

Purpose of the Study:

  • To develop a practical and high-yielding method for functionalizing the Csp³-F bond under mild conditions.
  • To achieve selective carbon-carbon bond formation with unactivated alkyl fluorides.
  • To demonstrate the broad applicability and functional group tolerance of the new method.

Main Methods:

  • Utilized cryogenic temperatures (as low as -78 °C) for Csp³-F bond cleavage.
  • Employed fluorophilic organoaluminum compounds to activate the C-F bond.
  • Leveraged fast nucleophile transfer of intermediate ate complexes for bond formation.

Main Results:

  • Achieved practical and high-yielding functionalization of primary, secondary, and tertiary alkyl fluorides.
  • Demonstrated exceptional chemoselectivity, tolerating a wide range of other functional groups.
  • Successfully forged new carbon-carbon bonds via arylation, alkylation, alkenylation, and alkynylation reactions.

Conclusions:

  • The developed method selectively targets the strong C-F bond, overcoming previous synthetic limitations.
  • This approach offers a complementary strategy for late-stage functionalization, expanding synthetic possibilities.
  • The stability of the Al-F bond serves as a key thermodynamic driver for the observed reactivity.