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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
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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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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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Defluorinative Functionalization of Pd(II) Fluoroalkyl Complexes.

Michael M Wade Wolfe1, James P Shanahan1, Jeff W Kampf1

  • 1Department of Chemistry, University of Michigan, 930 N. University, Ann Arbor, Michigan 48109, United States.

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|October 19, 2020
PubMed
Summary

This study introduces a novel defluorinative arylation reaction using palladium complexes. It efficiently converts fluoroalkyl palladium species into arylated products, expanding synthetic possibilities.

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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Palladium complexes are crucial in organic synthesis.
  • Defluorinative reactions are challenging but synthetically valuable.
  • Arylboranes are versatile coupling partners.

Purpose of the Study:

  • To develop a novel defluorinative arylation reaction.
  • To utilize anionic trifluoromethyl and difluorobenzyl palladium(II) complexes.
  • To enable the synthesis of diverse arylated compounds.

Main Methods:

  • Fluoride abstraction from palladium complexes using arylboranes.
  • 1,1-migratory insertion of fluoroalkyl groups.
  • Transmetalation and reductive elimination using fluoroboronates or boronic acids/esters.

Main Results:

  • A net defluorinative arylation reaction was achieved.
  • Structurally diverse substrates were synthesized.
  • The reaction can be performed using isolated palladium-CF3 complexes or readily available reagents.

Conclusions:

  • The developed method offers a new route for defluorinative arylation.
  • The reaction is versatile and applicable to various substrates.
  • This work expands the toolkit for organofluorine synthesis.