Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand.
Angew Chem Int Ed Engl
; 61(28): e202201240, 2022 07 11.
Article
em En
| MEDLINE
| ID: mdl-35502813
A two-step strategy for the transition-metal-free C-H functionalization of arenes using unsymmetrical iodonium salts as versatile synthetic linchpins is presented. The key to the success of this strategy is the identification of the 3,5-dimethyl-4-isoxazolyl (DMIX) group as a superior dummy ligand, which enables not only site-selective C-H functionalization to afford unsymmetrical iodonium salts, but also highly selective aryl transfer during the subsequent metal-free coupling reaction. Both electron-rich and moderately electron-deficient arenes can be converted into the iodonium salts through C-H functionalization, allowing for diverse structural elaboration by metal-free C-N, C-C, C-S, and C-O coupling.
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Angew Chem Int Ed Engl
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2022
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Article