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 Vladimirovich Zhdankin

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

(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
Pages (from-to)4831-4834
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number22
DOIs
Publication statusPublished - 1 Aug 2015

Keywords

  • Hypervalent compounds
  • Iodine
  • Silicon
  • Steric hindrance

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Fingerprint Dive into the research topics of 'Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryliodonium Salts'. Together they form a unique fingerprint.

Cite this