1616489-30-5Relevant articles and documents
Pd-catalyzed aerobic oxidative coupling of arenes: Evidence for transmetalation between two Pd(II)-aryl intermediates
Wang, Dian,Izawa, Yusuke,Stahl, Shannon S.
, p. 9914 - 9917 (2014)
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 PdX 2/2-fluoropyridine catalyst (X = trifluoroacetate, acetate). Kinetic studies, H/D exchange experiments, and kinetic isotope effects provide clear support for a bimetallic/transmetalation mechanism.