Synlett 2019; 30(07): 777-782
DOI: 10.1055/s-0037-1610347
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© Georg Thieme Verlag Stuttgart · New York

New Avenues in Radical Trifluoromethylselenylation with ­Trifluoromethyl Tolueneselenosulfonate

Clément Ghiazza
a  Institute 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
b  Univ Lyon, Ens de Lyon, CNRS UMR 5182, Université Lyon 1, Laboratoire de Chimie, F-69342, Lyon, France
,
Lhoussain Khrouz
b  Univ Lyon, Ens de Lyon, CNRS UMR 5182, Université Lyon 1, Laboratoire de Chimie, F-69342, Lyon, France
,
Maurice Médebielle
a  Institute 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
,
a  Institute 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
c  CERMEP-In vivo Imaging, Groupement Hospitalier Est, 59 Bd Pinel, F-69003, Lyon, France
,
a  Institute 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
› Author Affiliations
C.G. held a doctoral fellowship from la region Auvergne Rhône Alpes. The authors are grateful to the CNRS, ICBMS (UMR 5246), ICL (Institut de Chimie de Lyon) for financial support. The French Fluorine Network as well as the federation RENARD are also acknowledged for their support.
Further Information

Publication History

Received: 18 October 2018

Accepted after revision: 12 November 2018

Publication Date:
11 December 2018 (eFirst)

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

 
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