1 research outputs found
Mechanistic Study on Aryl-Exchange Reaction of Diaryl‑λ<sup>3</sup>‑iodane with Aryl Iodide
Because
of its hyper-leaving ability, as well as its strong oxidizing
ability, diarylÂ(triflato)-λ<sup>3</sup>-iodane transfers one
of the aryl groups to iodoarenes simply upon gentle heating (>85
°C)
in nonpolar solvents. We have performed an in-depth mechanistic study
of this unusual aryl transfer reaction. A combination of experimental
(product analysis, kinetic study, and substituent effects) and density
functional theoretical approaches revealed that the reaction proceeds
through a concerted bimolecular transition state, in which <i>ipso</i>-carbon binds loosely to both iodine centers. We also
evaluated electronic effects on the thermodynamic stability of diaryl-λ<sup>3</sup>-iodanes