Accumulation, Characterization and Reactivity of Chiral Ammonium-Carboxonium Dications in Superacid

Emanuela Berrino; Thomas Cantin; Maxime Artault; Stefanie Beck; Christoph Jessen; Jérôme Marrot; Frédéric Guégan; Agnès Mingot; Andreas Kornath; Sébastien Thibaudeau

doi:10.1002/anie.202404066

Accumulation, Characterization and Reactivity of Chiral Ammonium-Carboxonium Dications in Superacid

Angew Chem Int Ed Engl. 2024 Apr 8:e202404066. doi: 10.1002/anie.202404066. Online ahead of print.

Affiliations

¹ IC2MP UMR CNRS 7285, Université de Poitiers, 4 rue Michel, Brunet, 86073 Poitiers cedex 9, France.
² Department of Chemistry, Ludwig-Maximilian University of Munich, Butenandtstr. 5-13, D-81377, München, Germany.
³ UMR CNRS 8180, 45 avenue des États-Unis, 78035, Versailles Cedex, France.

PMID: 38587216
DOI: 10.1002/anie.202404066

Abstract

The accumulation of chiral ammonium-oxocarbenium dications in superacid is evidenced by low-temperature NMR spectroscopy, X-ray diffraction analysis and confirmed by DFT calculations. Its potential for the diastereoselective remote hydrofunctionalization of non-activated alkene is also explored.

Keywords: cations; fluorine; mechanisms; reaction; superelectrophile.