Preparation and structure of phenolic aryliodonium salts

Chemical Communications : Chem Comm
Akira YoshimuraViktor V Zhdankin

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.

References

Apr 27, 2002·The Journal of Organic Chemistry·Darren BykowskiRik R Tykwinski
Oct 31, 2009·Angewandte Chemie·Eleanor A Merritt, Berit Olofsson
Feb 11, 2016·Chemical Reviews·Akira Yoshimura, Viktor V Zhdankin
Aug 17, 2016·Angewandte Chemie·Gergely L TolnaiBerit Olofsson
Nov 3, 2016·Organic & Biomolecular Chemistry·Ming Wang, Zhijian Huang
Jun 15, 2017·Journal of the American Chemical Society·Tsugio KitamuraJuzo Oyamada
Oct 6, 2017·Journal of Labelled Compounds & Radiopharmaceuticals·Victor W Pike
Oct 6, 2017·Chemistry : a European Journal·Akira YoshimuraViktor V Zhdankin
Nov 17, 2017·Organic Letters·Raphaël RobidasClaude Y Legault
Mar 7, 2018·Beilstein Journal of Organic Chemistry·Huangguan ChenLimin Wang
May 26, 2018·Chemistry : a European Journal·Akira YoshimuraViktor V Zhdankin

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Citations

Jul 30, 2020·Organic & Biomolecular Chemistry·Ahmed M H AbudkenAlison M Stuart

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Methods Mentioned

BETA
X-ray

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