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The kinetics of the oxidative additions of haloheteroarenes HetX (X=I, Br, Cl) to Pd(0) (PPh3 )2 (generated from Pd(0) (PPh3 )4 ) have been investigated in THF and DMF and the rate constants have been determined. In contrast to the generally accepted concerted mechanism, Hammett plots obtained for substituted 2-halopyridines and solvent effects reveal a reaction mechanism dependent on the halide X of HetX: an unprecedented SN Ar-type mechanism for X=Br or Cl and a classical concerted mechanism for X=I. These results are supported by DFT studies.
Maes et al. (Wed,) studied this question.
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