Preparation and structure of phenolic aryliodonium salts

Akira Yoshimura, Michael T. Shea, Olga Guselnikova, Pavel S. Postnikov, Gregory T. Rohde, Akio Saito, Mekhman S. Yusubov, Victor N. Nemykin, Viktor Zhdankin

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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.

Original languageEnglish (US)
Pages (from-to)10363-10366
Number of pages4
JournalChemical Communications
Volume54
Issue number73
DOIs
StatePublished - Jan 1 2018

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    Yoshimura, A., Shea, M. T., Guselnikova, O., Postnikov, P. S., Rohde, G. T., Saito, A., Yusubov, M. S., Nemykin, V. N., & Zhdankin, V. (2018). Preparation and structure of phenolic aryliodonium salts. Chemical Communications, 54(73), 10363-10366. https://doi.org/10.1039/C8CC06211K