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Electron Affinity03:07

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sp3d and sp3d 2 Hybridization
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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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Electrochemical C(sp3)-H Fluorination.

Yusuke Takahira1, Miao Chen1, Yu Kawamata1

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
|March 26, 2021
PubMed
Summary
This summary is machine-generated.

A new electrochemical method enables alkyl C-H fluorination using a nitrate additive and Selectfluor. This robust technique efficiently converts various C-H bonds to C-F bonds, demonstrating scalability for practical applications.

Keywords:
C–H functionalizationelectrochemistryfluorinationorganic synthesisradical

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Fluorination Chemistry

Background:

  • C-H bond functionalization is crucial in organic synthesis.
  • Electrochemical methods offer sustainable alternatives for chemical transformations.
  • Direct C-H fluorination remains a significant challenge in synthetic chemistry.

Purpose of the Study:

  • To develop a simple and robust method for electrochemical alkyl C-H fluorination.
  • To explore the use of readily available reagents and carbon electrodes.
  • To demonstrate the scalability of the developed fluorination technique.

Main Methods:

  • Electrochemical oxidation of C-H bonds in the presence of a nitrate additive.
  • Utilizing Selectfluor as the fluorine source.
  • Employing carbon-based electrodes for the reaction.

Main Results:

  • Successful conversion of a wide range of activated and unactivated alkyl C-H bonds to C-F bonds.
  • The reaction proceeds under mild and simple conditions.
  • Demonstrated scalability with a 100-gram synthesis of fluorovaline.

Conclusions:

  • The presented electrochemical method provides an efficient route for C-H fluorination.
  • The use of nitrate additives and carbon electrodes simplifies the process.
  • The method's scalability indicates its potential for industrial applications.