Leveraging long-lived arenium ions in superacid for meta-selective methylation

Autor: Paul Bourbon, Kassandra Vitse, Agnès Martin-Mingot, Hugo Geindre, Frédéric Guégan, Bastien Michelet, Sébastien Thibaudeau

Publikováno v: Nature Communications, Vol 15, Iss 1, Pp 1-10 (2024)

Abstract Electrophilic aromatic substitution is one of the most mechanistically studied reactions in organic chemistry. However, precluded by innate substituent effects, the access to certain substitution patterns remains elusive. While selective C�

Externí odkaz: https://doaj.org/article/ff1f36c124ea457eaf96656b8a8109c1

Exploring F/CF3 substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans

Autor: Anthony J. Fernandes, Bastien Michelet, Armen Panossian, Agnès Martin-Mingot, Frédéric R. Leroux, Sébastien Thibaudeau

Publikováno v: Chemical Communications. 59:4083-4086

We report on the dramatic effect of a local partial charge inversion by replacing a CHCH3 group by a CFCF3. This strategy allows the diastereoselective reduction of 5-membered ring oxocarbenium ions to access highly substituted tetrahydrofurans.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::5afce090c39b6c6a2b6aad11c19db5d0
https://doi.org/10.1039/d2cc06521e

Modulating the Efficacy of Carbonic Anhydrase Inhibitors through Fluorine Substitution

Autor: Claudiu T. Supuran, Emanuela Berrino, Sébastien Thibaudeau, Bastien Michelet, Fabrizio Carta, Agnès Martin-Mingot

Publikováno v: Angewandte Chemie International Edition
Angewandte Chemie International Edition, Wiley-VCH Verlag, In press, ⟨10.1002/anie.202103211⟩

International audience; The insertion of fluorine atoms and/or fluoroalkyl groups can lead to many beneficial effects in biologically active molecules, such as enhanced metabolic stability, bioavailability, lipophilicity, and membrane permeability, a

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b04ab68f4948f2c6140ca604e7382d4b
https://doi.org/10.1002/ange.202103211

Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids

Autor: Jérôme Désiré, Naresh Bhuma, Agnès Martin-Mingot, Jesús Jiménez-Barbero, Bastien Michelet, Yves Blériot, Zahra Abada, Aiichiro Nagaki, Sébastien Thibaudeau, Jérôme Marrot, Ludivine Lebedel, Ana Ardá, Masahiro Takumi, Hiroki Yamashita, Ali Abou-Hassan, Yutaka Shimizu

Publikováno v: Angewandte Chemie International Edition
Angewandte Chemie International Edition, Wiley-VCH Verlag, 2021, 60 (4), pp.2036-2041. ⟨10.1002/anie.202010175⟩

International audience; The transformation of glycals into 2,3-unsaturated glycosyl derivatives, reported by Ferrier in 1962, is supposed to involve an α,β unsaturated glycosyl cation, an elusive ionic species that has still to be observed experime

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::00e3faebd507ea16cb5c14e2df33c14e
https://doi.org/10.1002/ange.202010175

Superelectrophilic Csp3–H bond fluorination of aliphatic amines in superacid: the striking role of ammonium–carbenium dications

Autor: Agnès Martin-Mingot, Sébastien Thibaudeau, M. Artault, Naima Mokhtari, Thomas Cantin

Publikováno v: Chemical Communications. 56:5905-5908

The superacid-promoted electrophilic Csp3–H bond activation of aliphatic amines generates superelectrophilic species that can be subsequently fluorinated. Demonstrated by low-temperature in situ NMR experiments, the ammonium–carbenium dications,

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::175a468ad2946a89993eda22c63712c2
https://doi.org/10.1039/d0cc02081h