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Keywords:

  • copper;
  • cross-coupling;
  • isotopic labeling;
  • NMR spectroscopy;
  • S ligands
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CuIIIin focus: The key intermediate in copper-mediated cross-coupling reactions has long been believed to be a “copper(III) intermediate”. Investigation of reactions of a variety of methyl Gilman reagents Me2CuLi⋅LiX with EtI using rapid-injection NMR spectroscopy conditions reveals a number of formally CuIII tetracoordinate square-planar intermediates (see scheme) with a surprising range of stabilities.