Radical photochemical difluorosulfoximination of alkenes and propellanes

Herein, we report a metal-free divergent visible-light driven method for the synthesis of fluorinated sulfoximines. Both olefins and propellanes efficiently undergo difluorosulfoximination with yields up to 77% (65 examples). The process is general and robust and tolerates diverse functional groups, including esters, ethers, ketones, silyl groups, silyl ethers or boronic esters. The functionalization of diverse bioactive ingredients (8 examples) and various product manipulations demonstrate the synthetic usefulness of the developed synthetic platform. Finally, we rationalized the divergent reaction mechanism by performing Stern-Volmer quenching and EPR experiments that revealed the key activity of a difluoroalkyl sulfoximine radical.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc01068c
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.58

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article

Radical photochemical difluorosulfoximination of alkenes and propellanes

Giorgio Pelosi, Luca Dell’Amico, Guillaume Dagousset, Elsa Anselmi et al.
2 citations
Chemical Science
Fluorine in Organic Chemistry
1.58
article

Radical photochemical difluorosulfoximination of alkenes and propellanes

Giorgio Pelosi, Luca Dell’Amico, Guillaume Dagousset, Elsa Anselmi, Sara Cuadros, Julien Paut, Simone Baldon, Emmanuel Magnier, Béatrice Tuccio
article en
2 citations

Abstract

Herein, we report a metal-free divergent visible-light driven method for the synthesis of fluorinated sulfoximines. Both olefins and propellanes efficiently undergo difluorosulfoximination with yields up to 77% (65 examples). The process is general and robust and tolerates diverse functional groups, including esters, ethers, ketones, silyl groups, silyl ethers or boronic esters. The functionalization of diverse bioactive ingredients (8 examples) and various product manipulations demonstrate the synthetic usefulness of the developed synthetic platform. Finally, we rationalized the divergent reaction mechanism by performing Stern-Volmer quenching and EPR experiments that revealed the key activity of a difluoroalkyl sulfoximine radical.

Chemical ScienceVol. 16(16)
Université de Tours (FR), University of Parma (IT), Centre National de la Recherche Scientifique (FR), University of Padua (IT), Aix-Marseille Université (FR), Université Paris-Saclay (FR), Centrale Méditerranée (FR), Institut Lavoisier de Versailles (FR)
Università degli Studi di Padova, Centre National de la Recherche Scientifique, Université Paris-Saclay, National Institute of Environmental Health Sciences
Openalex Percentile: Top 18%
Fluorine in Organic Chemistry
1.58
DOIOpen Access PDFOpenAlex
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Radical photochemical difluorosulfoximination of alkenes and propellanes — Giorgio Pelosi, Luca Dell’Amico, et al. · Chemical Science (2025) | TGRS Research Map | TGRS