Predestined to be transient theoretical species, phenonium ions can now be considered as cationic intermediates of choice in organic synthesis. Here, we demonstrate that under non-nucleophilic and superacidic conditions, CF-substituted phenonium ions can be generated to furnish original CF-substituted dihydrostilbenes of interest.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9036966 | PMC |
http://dx.doi.org/10.1039/d1ra04901a | DOI Listing |
Angew Chem Int Ed Engl
October 2024
Institut de Science et d'Ingénierie Supramoléculaires (ISIS) CNRS UMR 7006, Université de Strasbourg, 8 Allée Gaspard Monge, 67000, Strasbourg, France.
The catalytic deoxyamination of readily available 2-arylethanols offers an appealing, simple, and straightforward means of accessing β-(hetero)arylethylamines of biological interest. Yet, it currently represents a great challenge to synthetic chemistry. In most cases, the alcohol has to be either pre-activated in situ or converted into a reactive carbonyl intermediate, limiting the substrate scope for some methods.
View Article and Find Full Text PDFRSC Adv
July 2021
IC2MP, UMR CNRS 7285, Equipe "Synthèse Organique", Université de Poitiers 4 rue Michel Brunet 86073 Poitiers Cedex 9 France.
Predestined to be transient theoretical species, phenonium ions can now be considered as cationic intermediates of choice in organic synthesis. Here, we demonstrate that under non-nucleophilic and superacidic conditions, CF-substituted phenonium ions can be generated to furnish original CF-substituted dihydrostilbenes of interest.
View Article and Find Full Text PDFOrg Lett
January 2022
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
We report that the treatment of unsymmetrical 2,3-disubstituted aziridines with TiCl yields β-phenethylamine products via the intermediacy of a phenonium ion. Derivatization of the products obtained via this method is demonstrated. Computational analysis of the reaction pathway provides insight into the reaction mechanism, including the selectivity of the phenonium opening.
View Article and Find Full Text PDFJ Am Chem Soc
May 2020
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
We report the first examples of selective and regiodivergent opening of unsymmetrical phenonium ions with chloride ions. These reactions are enabled by the dual role of SnCl and TiCl as Lewis acids and chloride nucleophiles. Reagent control dictates addition of chloride at either the substituted internal position (SnCl) or unsubstituted terminal position (TiCl) of the phenonium ion.
View Article and Find Full Text PDFJ Phys Org Chem
November 2016
Department of Chemistry, University at Buffalo, SUNY, Buffalo, NY 14260, USA.
The results of studies on the structure and reactivity of spiro[5.2]oct-5,7-diene-4yl carbocation [phenonium ion] have had a significant impact on the course of discussion about the distinction between classical and nonclassical carbocations. This minireview will present a brief overview of the structure, bonding and reactivity of ring substituted phenonium ions (), with an emphasis on work completed since 2004.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!