Fe-mediated nucleophilic trifluoromethylselenolation of activated alkyl bromides via umpolung reactivity of trifluoromethyl tolueneselenosulfinate

Kevin Grollier (1) , Emmanuel Chefdeville (1) , Arnaud de Zordo-Banliat (2) , Bruce Pegot (2) , Guillaume Dagousset (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

Trifluoromethyl tolueneselenosulfonate is a versatile reagent which can be reduced by iron powder to generate in situ trifluoromethylselenolate anion. This species can then react with alkyl bromide to perform SN2 reaction.

Mots clés: Fluorine; Selenium; Trifluoromethylselenolation; Iron

Domaines: Chimie organique

Kevin Grollier, Emmanuel Chefdeville, Arnaud de Zordo-Banliat, Bruce Pegot, Guillaume Dagousset, et al.. Fe-mediated nucleophilic trifluoromethylselenolation of activated alkyl bromides via umpolung reactivity of trifluoromethyl tolueneselenosulfinate. Tetrahedron, 2021, 100, pp.132498. ⟨10.1016/j.tet.2021.132498⟩. ⟨hal-03834329⟩