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 V. Zhdankin

Research output: Contribution to journalArticle

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
Pages (from-to)10363-10366
Number of pages4
JournalChemical Communications
Volume54
Issue number73
DOIs
Publication statusPublished - 1 Jan 2018

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Salts
X ray crystallography
Phenol
Phenols
Nucleophiles
Ethers
Iodine
Single crystals
Acids

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Preparation and structure of phenolic aryliodonium salts. / Yoshimura, Akira; Shea, Michael T.; Guselnikova, Olga; Postnikov, Pavel S.; Rohde, Gregory T.; Saito, Akio; Yusubov, Mekhman S.; Nemykin, Victor N.; Zhdankin, Viktor V.

In: Chemical Communications, Vol. 54, No. 73, 01.01.2018, p. 10363-10366.

Research output: Contribution to journalArticle

Yoshimura, Akira ; Shea, Michael T. ; Guselnikova, Olga ; Postnikov, Pavel S. ; Rohde, Gregory T. ; Saito, Akio ; Yusubov, Mekhman S. ; Nemykin, Victor N. ; Zhdankin, Viktor V. / Preparation and structure of phenolic aryliodonium salts. In: Chemical Communications. 2018 ; Vol. 54, No. 73. pp. 10363-10366.
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