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

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

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88. Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate.pdf (225.15 Ko)

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https://hal.science/hal-03097741

Soumis le : mardi 5 janvier 2021-14:41:47

Dernière modification le : lundi 16 décembre 2024-15:40:03

Archivage à long terme le : mercredi 7 avril 2021-09:21:48

Dates et versions

hal-03097741 , version 1 (05-01-2021)

Identifiants

HAL Id : hal-03097741 , version 1
DOI : 10.3762/bjoc.16.252

Citer

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⟩

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