New Avenues in Radical Trifluoromethylselenylation with ­Trifluoromethyl Tolueneselenosulfonate

Clément Ghiazza; Cyrille Monnereau; Lhoussain Khrouz; Maurice Médebielle; Thierry Billard; Anis Tlili

doi:10.1055/s-0037-1610347

Synlett, Table of Contents

Synlett 2019; 30(07): 777-782
DOI: 10.1055/s-0037-1610347

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New Avenues in Radical Trifluoromethylselenylation with Trifluoromethyl Tolueneselenosulfonate

Clément Ghiazza

^aInstitute of Chemistry and Biochemistry (ICBMS–UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France Email: anis.tlili@univ-lyon1.fr

,

Cyrille Monnereau

^bUniv Lyon, Ens de Lyon, CNRS UMR 5182, Université Lyon 1, Laboratoire de Chimie, F-69342, Lyon, France

,

Lhoussain Khrouz

^bUniv Lyon, Ens de Lyon, CNRS UMR 5182, Université Lyon 1, Laboratoire de Chimie, F-69342, Lyon, France

,

Maurice Médebielle

^aInstitute of Chemistry and Biochemistry (ICBMS–UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France Email: anis.tlili@univ-lyon1.fr

,

Thierry Billard *

^aInstitute of Chemistry and Biochemistry (ICBMS–UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France Email: anis.tlili@univ-lyon1.fr

^cCERMEP-In vivo Imaging, Groupement Hospitalier Est, 59 Bd Pinel, F-69003, Lyon, France

,

Anis Tlili *

^aInstitute of Chemistry and Biochemistry (ICBMS–UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France Email: anis.tlili@univ-lyon1.fr

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Abstract

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Published as part of the Special Section 10th EuCheMS Organic Division Young Investigator Workshop

Abstract

We demonstrated that the shelf-stable reagent trifluoromethyl tolueneselenosulfonate can be involved in radical trifluoromethylselenylation. Upon visible-light irradiation, the homolysis of the reagent could take place at room temperature. This finding is explored for unprecedented C(sp²)–SeCF₃ and C(sp³)–SeCF₃ processes under transition-metal-free conditions. Mechanistic investigations, including cyclic voltammetry, luminescence measurement, and EPR studies, allowed the proposal of plausible mechanisms.

1 Introduction.

2 Reactivity of Reagent I with Diazonium Salts

3 Reactivity of Reagent I with Alkenes and Alkynes

4 Conclusion

Key words

trifluoromethylselenylation - trifluoromethyl tolueneselenosulfonate - arenediazonium salts - eosin Y - photochemistry - radical reactions

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References

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New Avenues in Radical Trifluoromethylselenylation with ­Trifluoromethyl Tolueneselenosulfonate

New Avenues in Radical Trifluoromethylselenylation with Trifluoromethyl Tolueneselenosulfonate