1. Mechanistic Study on Aryl-Exchange Reaction of Diaryl-λ³-iodane with Aryl Iodide.
- Author
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Yui Masumoto, Kazunori Miyamoto, Takuto Iuchi, Masahito Ochiai, Keiichi Hirano, Tatsuo Saito, Chao Wang, and Masanobu Uchiyama
- Abstract
Because of its hyper-leaving ability, as well as its strong oxidizing ability, diaryl(triflato)-λ³-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 ipso-carbon binds loosely to both iodine centers. We also evaluated electronic effects on the thermodynamic stability of diaryl-λ³-iodanes. [ABSTRACT FROM AUTHOR]
- Published
- 2018
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