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Controlling selectivity in the Ullmann reaction on Cu(111).

E A Lewis1, M D Marcinkowski, C J Murphy

  • 1Department of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA 02155, USA. Charles.sykes@tufts.edu.

Chemical Communications (Cambridge, England)
|June 28, 2017
PubMed
Summary
This summary is machine-generated.

Selectivity in Ullmann cross-coupling reactions on copper surfaces is controlled by reactant binding and repulsion. Maximizing cross-coupling efficiency is achieved by using low reactant concentrations.

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Area of Science:

  • Surface science
  • Organometallic chemistry
  • Catalysis

Background:

  • The Ullmann cross-coupling reaction is a vital method for forming carbon-carbon bonds.
  • Controlling selectivity in these reactions on metal surfaces remains a challenge.

Purpose of the Study:

  • To understand and control the selectivity of aryl halide Ullmann cross-coupling on a Cu(111) surface.
  • To elucidate the factors governing intermediate formation and product distribution.

Main Methods:

  • Utilized a surface science approach to study the Ullmann cross-coupling reaction.
  • Investigated the influence of reactant binding strength and intermolecular repulsion on Cu(111).

Main Results:

  • Demonstrated that binding strength and reactant repulsion dictate organometallic intermediate formation.
  • Showed that product distribution is directly influenced by these surface interactions.
  • Identified low reactant concentrations as a condition to maximize cross-coupling.

Conclusions:

  • Surface science provides a powerful platform for understanding and controlling catalytic reactions.
  • The Ullmann cross-coupling on Cu(111) can be optimized by managing reactant interactions at the surface.
  • Low concentrations are key to enhancing cross-coupling yields.