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Issue 73, 2018
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Preparation and structure of phenolic aryliodonium salts

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Abstract

Phenol based aryliodonium salts were prepared by the reaction of [hydroxy(tosyloxy)iodo]arenes with aryl silyl ethers in the presence of trifluoromethanesulfonic acid. Structures of several aryliodonium salts with the hydroxy group in the para-position of the phenyl ring were established by single crystal X-ray crystallography. Under basic conditions, 4-hydroxyphenyl(phenyl)iodonium salts form a dimeric hypervalent iodine(III) complex, oxyphenyl(phenyl)iodonium ylidic salt, the solid structure of which was confirmed by X-ray crystallography. Phenolic iodonium salts are potentially useful phenol transfer reagents in reactions with various anionic nucleophiles.

Graphical abstract: Preparation and structure of phenolic aryliodonium salts

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Supplementary files

Article information


Submitted
30 Jul 2018
Accepted
17 Aug 2018
First published
22 Aug 2018

Chem. Commun., 2018,54, 10363-10366
Article type
Communication
Author version available

Preparation and structure of phenolic aryliodonium salts

A. Yoshimura, M. T. Shea, O. Guselnikova, P. S. Postnikov, G. T. Rohde, A. Saito, M. S. Yusubov, V. N. Nemykin and V. V. Zhdankin, Chem. Commun., 2018, 54, 10363
DOI: 10.1039/C8CC06211K

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