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

Kevin Grollier; Alexis Taponard; Arnaud De Zordo-Banliat; Emmanuel Magnier; Thierry Billard

doi:10.3762/bjoc.16.252

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

Beilstein J Org Chem. 2020 Dec 10:16:3032-3037. doi: 10.3762/bjoc.16.252. eCollection 2020.

Authors

Kevin Grollier^#¹, Alexis Taponard^#¹, Arnaud De Zordo-Banliat², Emmanuel Magnier², Thierry Billard^{1

3}

Affiliations

¹ Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE, INSA, 43 Bd du 11 novembre 1918, 69622 Villeurbanne, France.
² Université Paris-Saclay, UVSQ, CNRS, UMR 8180, Institut Lavoisier de Versailles, 78035 Versailles Cedex, France.
³ CERMEP-In vivo imaging, Groupement Hospitalier Est, 59 Bd Pinel, 69677 Lyon, France.

^# Contributed equally.

Abstract

We report herein a practical method to generate CF₃Se^- (and R_FSe^-) 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.

Keywords: fluorine; nucleophilic substitution; perfluoroalkylselenolation; selenium; trifluoromethylselenolation.

Grants and funding

This work was supported by a grant from the French National Research Agency (ANR 18-CE07-0039-01). The authors are grateful to the CNRS and the French Ministry of Research for financial support. The French Fluorine Network is also acknowledged for its support.