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

Wei Ding, Chen Wang, Jie Ren Tan, Chang Chin Ho, Felix León, Felipe García, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)7356-7361
Number of pages6
JournalChemical Science
Volume11
Issue number28
DOIs
Publication statusPublished - 2020 Jun 28
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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