Site-selective aromatic C-H λ3-iodanation with a cyclic iodine(iii) electrophile in solution and solid phases.

Chemical Science
Wei DingNaohiko Yoshikai

Abstract

An efficient and site-selective aromatic C-H λ3-iodanation reaction is achieved using benziodoxole triflate (BXT) as an electrophile under room temperature conditions. The reaction tolerates a variety of electron-rich arenes and heteroarenes to afford the corresponding arylbenziodoxoles in moderate to good yields. The reaction can also be performed mechanochemically by grinding a mixture of solid arenes and BXT under solvent-free conditions. The arylbenziodoxoles can be used for various C-C and C-heteroatom bond formations, and are also amenable to further modification by electrophilic halogenation. DFT calculations suggested that the present reaction proceeds via a concerted λ3-iodanation-deprotonation transition state, where the triflate anion acts as an internal base.

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Citations

Jan 14, 2021·Organic Letters·Roshayed Ali LaskarNaohiko Yoshikai
Apr 10, 2021·ChemSusChem·Karen J Ardila-Fierro, José G Hernández

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Methods Mentioned

BETA
NMR
X-ray

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