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 language | English (US) |
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Pages (from-to) | 4831-4834 |
Number of pages | 4 |
Journal | European Journal of Organic Chemistry |
Volume | 2015 |
Issue number | 22 |
DOIs | |
State | Published - Aug 1 2015 |
Bibliographical note
Publisher Copyright:Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Keywords
- Hypervalent compounds
- Iodine
- Silicon
- Steric hindrance