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. 2025 Apr 7;64(15):e202423857.
doi: 10.1002/anie.202423857. Epub 2025 Jan 28.

Halogenated Trityl Cations as Easy-to-Access Super Electrophiles

Johanna Schlögl  1 , Amelie L Brosius  1 , Ahmet N Toraman  1 , Anja Wiesner  1 , Simon Steinhauer  1 , Carsten Müller  1 , Sebastian Riedel  1
Affiliations

Halogenated Trityl Cations as Easy-to-Access Super Electrophiles

Johanna Schlögl et al. Angew Chem Int Ed Engl. .

Abstract

Herein, we present the easy-to-access synthesis of the perfluorotrityl cation (15F+) with commercial GaCl3 and the further functionalization of the para-fluorine atoms of 15F+ via halodefluorination using trimethylsilyl halides TMSX (X=Cl, Br). This gives access to equally reactive halogenated trityl derivatives (p-3Cl12F+ and p-3Br12F+), which can be handled at room temperature. The impact of the para-exchange on the electronic structure is determined by NMR and UV/Vis spectroscopy. Finally, the new synthons' high hydride ion affinities are demonstrated computationally and experimentally by hydride abstraction from the short-chain, linear alkanes n-pentane and n-butane.

Keywords: carbocations; hydride abstraction; strong electrophiles; strong oxidizers; trityl cations.

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