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Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand.

Yixuan ChenYuefei GuHuan MengQianzhen ShaoZhenchuang XuWenjing BaoYucheng GuXiao-Song XueYanchuan Zhao
Published in: Angewandte Chemie (International ed. in English) (2022)
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.
Keyphrases
  • ionic liquid
  • electron transfer
  • room temperature
  • molecularly imprinted
  • solar cells
  • mass spectrometry
  • electron microscopy