A Shelf‐Stable Reagent for Photocatalytic Radical Pentafluorosulfanylation of Styrene Derivatives
We have developed the first family of air- and moisture-stable pentafluorosulfanylation (SF₅) reagents. Although the SF₅ group is a bioisostere of the trifluoromethyl group (CF₃)-exhibiting even greater electronegativity and lipophilicity, attributes that have earned it the nickname "super trifluoromethyl group"-the development of shelf-stable, non-toxic, and easy-to-handle SF₅-incorporating reagents had remained elusive for over 70 years since its discovery. Our discovery enables the synthesis of per- and polyfluoroalkyl substances (PFAS)-free fluorinated compounds, offering significant advantages over traditional CF₃ analogs. These new reagents exhibit promising reactivity under photochemical conditions, efficiently facilitating the formation of novel SF₅-containing molecules. Moreover, our approach is compatible with the late-stage functionalization of complex molecules. Mechanistic studies have provided valuable insights into the underlying reaction pathways.
Authors
- Christophe Bucher (ORCID: https://orcid.org/0000-0003-1803-6733)
- Lhoussain Khrouz (ORCID: https://orcid.org/0000-0001-7098-8534)
- Anis Tlili (ORCID: https://orcid.org/0000-0002-3058-2043)
- Maurice Médebielle (ORCID: https://orcid.org/0000-0002-6032-4790)
- Alexis Taponard (ORCID: https://orcid.org/0000-0001-8008-2293)
- Yi Yang (ORCID: https://orcid.org/0000-0003-2797-8298)
- HAN Lulu
- Monnereau Cyrille
Institutions
- Université Claude Bernard Lyon 1 (FR)
- École Normale Supérieure de Lyon (FR)
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (FR)
- Laboratoire Hydrazines et Composés Energétiques Polyazotés (FR)
- Laboratoire de Chimie (FR)
- Institut National des Sciences Appliquées de Lyon (FR)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-05-02
- DOI
- https://doi.org/10.1002/anie.202505146
- Citations
- 16
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 12.65
Funders
- European Commission
- Agence Nationale de la Recherche
- China Scholarship Council
- Centre National de la Recherche Scientifique
- Horizon 2020 Framework Programme