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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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Publication details

The article was received on 30 Jul 2018, accepted on 17 Aug 2018 and first published on 22 Aug 2018


Article type: Communication
DOI: 10.1039/C8CC06211K
Citation: Chem. Commun., 2018,54, 10363-10366

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    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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