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

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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.

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

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Article information


Submitted
13 May 2020
Accepted
21 Jun 2020
First published
23 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

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

W. Ding, C. Wang, J. R. Tan, C. C. Ho, F. León, F. García and N. Yoshikai, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02737E

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