Skip to Main content Skip to Navigation
Journal articles

Oxidative Addition of Haloheteroarenes to Palladium(0): Concerted versus S N Ar-Type Mechanism

Abstract : 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 SNAr-type mechanism for X=Br or Cl and a classical concerted mechanism for X=I. These results are supported by DFT studies.
Document type :
Journal articles
Complete list of metadatas

https://hal-cea.archives-ouvertes.fr/cea-01635498
Contributor : Serge Palacin <>
Submitted on : Wednesday, November 15, 2017 - 11:39:50 AM
Last modification on : Wednesday, November 18, 2020 - 2:28:35 PM

Links full text

Identifiers

Citation

Bert U.W. Maes, Stefan Verbeeck, Tom Verhelst, Audrey Ekomié, Niklas Von wolff, et al.. Oxidative Addition of Haloheteroarenes to Palladium(0): Concerted versus S N Ar-Type Mechanism. Chemistry - A European Journal, Wiley-VCH Verlag, 2015, 21 (21), pp.7858 - 7865. ⟨10.1002/chem.201406210⟩. ⟨cea-01635498⟩

Share

Metrics

Record views

608