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Ladder diagrams are useful tools for understanding redox equilibrium reactions, especially the effects of concentration changes on the electrochemical potential of the reaction. The vertical axis in the redox ladder diagrams represents the electrochemical potential, E. The area of predominance is demarcated using the Nernst equation.
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Cross-Coupling through Ag(I)/Ag(III) Redox Manifold.

Luca Demonti1, Nathalie Saffon-Merceron2, Nicolas Mézailles1

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Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 2, 2021
PubMed
Summary
This summary is machine-generated.

Silver (Ag) can catalyze trifluoromethylation reactions via a Ag(I)/Ag(III) redox cycle, challenging the notion that silver is only an additive. This study demonstrates silver

Keywords:
AgIII chemistrycross-couplingfluorinehigh-valent speciestrifluoromethylation

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Silver (Ag) is often used as an additive in metal-catalyzed cross-coupling reactions.
  • Its role as a catalytically active species, particularly in redox processes, is frequently overlooked.
  • Misconceptions about silver's inability to undergo 2e- redox steps limit its exploration in catalysis.

Purpose of the Study:

  • To provide definitive proof of silver's capability in redox catalysis.
  • To investigate the Ag(I)/Ag(III) redox cycle for the oxidative trifluoromethylation of arenes.
  • To challenge the prevailing view of silver's limited role in cross-coupling reactions.

Main Methods:

  • Demonstration of facile Ag(I)/Ag(III) 2e- oxidation mediated by air.
  • Characterization of novel organosilver(III) compounds.
  • Utilizing silver(III) intermediates for cross-coupling reactions.

Main Results:

  • Established the elementary steps for Ag(I)/Ag(III) redox catalysis in arene trifluoromethylation.
  • Synthesized and fully characterized key organosilver(III) intermediates, including [K]+[Ag(III)(CF3)4]- (K-1), [(bpy)Ag(III)(CF3)3] (2), and [(phen)Ag(III)(CF3)3] (3).
  • Showcased the utility of compound 3 in cross-coupling, enabling the trifluoromethylation of diverse arylboron compounds via [Ag(III)(aryl)(CF3)3]- intermediates.

Conclusions:

  • Silver actively participates in redox catalysis, specifically in trifluoromethylation reactions.
  • The study provides concrete evidence for silver's catalytic competence in cross-coupling, utilizing a Ag(I)/Ag(III) redox mechanism.
  • This research overturns long-held assumptions about silver's limitations in undergoing cross-coupling reactions independently.