Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate

Kevin Grollier (1) , Alexis Taponard (1) , Arnaud de Zordo-Banliat (2) , Emmanuel Magnier (2) , Thierry Billard (1, 3)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 ILV - Institut Lavoisier de Versailles
3 CERMEP - imagerie du vivant - Centre d'Etude et de Recherche Multimodal Et Pluridisciplinaire en imagerie du vivant

We report herein a practical method to generate CF 3 Se − (and R F Se −) anions from shelf-stable reagents under iodide activation. Metal-free nucleophilic trifluoromethylselenolations have been then performed with this in situ-generated anion. Perfluoroalkylselenolations have also been described.

Mots clés: fluorine; nucleophilic substitution; perfluoroalkylselenolation; selenium; trifluoromethylselenolation

Domaines: Chimie organique

Kevin Grollier, Alexis Taponard, Arnaud de Zordo-Banliat, Emmanuel Magnier, Thierry Billard. Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate. Beilstein Journal of Organic Chemistry, 2020, 16, pp.3032 - 3037. ⟨10.3762/bjoc.16.252⟩. ⟨hal-03097741⟩