Pd-catalyzed aerobic oxidative coupling of arenes: Evidence for transmetalation between two Pd(II)-aryl intermediates

  • Wang D
  • Izawa Y
  • Stahl S
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Abstract

Pd-catalyzed aerobic oxidative coupling of arenes provides efficient access to biaryl compounds. The biaryl product forms via C–H activation of two arenes to afford a PdIIArAr′ intermediate, which then undergoes C–C reductive elimination. The key PdIIArAr′ intermediate could form via a “monometallic” pathway involving sequential C–H activation at a single PdII center, or via a “bimetallic” pathway involving parallel C–H activation at separate PdII centers, followed by a transmetalation step between two PdII–aryl intermediates. Here, we investigate the oxidative coupling of o-xylene catalyzed by a PdX2/2-fluoropyridine catalyst (X = trifluoroacetate, acetate). Kinetic studies, H/D exchange experiments, and kinetic isotope effects provide clear support for a bimetallic/transmetalation mechanism.

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Authors

  • Dian Wang

  • Yusuke Izawa

  • Shannon S. Stahl

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