Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryliodonium Salts

Mekhman S. Yusubov, Dmitrii Yu Svitich, Akira Yoshimura, Brent J. Kastern, Victor N. Nemykin, Viktor Zhdankin

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8 Scopus citations


(4-Triisopropylsilylphenyl)phenyliodonium tosylate, an aryliodonium salt bearing an extremely bulky, electron-donating triisopropylsilyl (TIPS) substituent in the phenyl ring, was prepared by the reaction of (4-tributyltinphenyl)triisopropylsilane with [hydroxy(tosyloxy)iodo]benzene (Koser's reagent). The TIPS-substituted aryliodonium tosylate was further converted into (4-triisopropylsilylphenyl)phenyliodonium bromide, the structure of which was established by single-crystal X-ray diffraction. Reactions of the TIPS-substituted arylodonium tosylate with bromide, azide, and thiocyanate anions predominantly afforded products of nucleophilic substitution in the electron-rich aromatic ring bearing the TIPS substituent. This unusual result is explained by the steric effect of the extraordinary bulky para-TIPS substituent on the configuration of the reaction intermediate.

Original languageEnglish (US)
Pages (from-to)4831-4834
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number22
StatePublished - Aug 1 2015

Bibliographical note

Publisher Copyright:
Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


  • Hypervalent compounds
  • Iodine
  • Silicon
  • Steric hindrance


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