Related Experiment Video
Updated: Jun 5, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Nucleophilic Fluorination of closo-Decaborate Iodonium Derivatives
Nikolay Neumolotov1, Vasilii Korotenko2,3, Vera Voinova1
1Kurnakov Institute of General and Inorganic Chemistry RAS, Moscow 119991, Russia.
Abstract:
New fluoroderivatives of the closo-decaborate anion with the composition [1,10-B10H8FX]n- (where X = IPh, Pyridine, I, Br, Cl, F, OH, CN) as well as [1-F, 6-NH3B10H8]- have been obtained. It was found that uncharged bisphenyliodonium derivative [1,10-(IPh)2B10H8]0 undergoes a nucleophilic substitution with the [K(18-crown-6)]+F- complex to form monofluoro derivative [1-IPh, 10-FB10H8]-, whereas the anionic Bu4N[1-B10H9IPh] does not react with the complex. This charge-dependent reactivity, as well as solvent effects, was explained using DFT and QTAIM calculations, revealing the crucial role of iodine sigma-hole availability and competitive solvation. The structures of the key products were confirmed by multinuclear NMR spectroscopy and single-crystal X-ray diffraction.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
12:27Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
ortho–para-Directing Deactivators: Halogens
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Hydroboration-Oxidation of Alkenes
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.