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PreprintCC BY-NC-NDChemRxiv

Redox-Paired Activation of Sulfur Hexafluoride Enables Nucleophilic C(sp3)–F Bond Formation

  • Aniruddha Biswas1,2,3
  • Demetra Zambardino2,3
  • Tanja Gulder1,2,3,4
4 affiliations
  1. 1Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) Helmholtz Center for Infection Research (HZI
  2. 2Organic Chemistry – Biomimetic Catalysis
  3. 3Saarland University
  4. 4Pharma Science Hub
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Abstract

Sulfur hexafluoride (SF6) is a potent greenhouse gas whose direct use as a fluorine source in organic synthesis remains underdeveloped. Here, we disclose complementary photoredox and electrochemical strategies for nucleophilic fluorinations with SF6, merging oxidative formation of carbocation intermediated from alkoxamines, carboxylic acids, or thiols with SF6 reduction, the latter providing fluoride for C(sp3)–F bond formation. The photochemical protocol efficiently converts electronrich substrates and tolerates a broad range of functional groups, whereas paired electrolysis extends the reaction to electronically deactivated substrates. Together, the two methods enable fluorination of diverse benzylic and aliphatic substrates, including late-stage fluorination of structurally complex derivatives of pharmaceuticals, natural products, and agrochemicals.

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Cite

BibTeXRIS
BibTeX
@misc{biswas2026redoxpaired,
  title = {{Redox-Paired Activation of Sulfur Hexafluoride Enables Nucleophilic C(sp3)–F Bond Formation}},
  author = {Aniruddha Biswas and Demetra Zambardino and Tanja Gulder},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15009734/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009734/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Redox-Paired Activation of Sulfur Hexafluoride Enables Nucleophilic C(sp3)–F Bond Formation
AU  - Aniruddha Biswas
AU  - Demetra Zambardino
AU  - Tanja Gulder
PY  - 2026
DA  - 2026/10/01
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009734/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009734/v1
AB  - Sulfur hexafluoride (SF6) is a potent greenhouse gas whose direct use as a fluorine source in organic synthesis remains underdeveloped. Here, we disclose complementary photoredox and electrochemical strategies for nucleophilic fluorinations with SF6, merging oxidative formation of carbocation intermediated from alkoxamines, carboxylic acids, or thiols with SF6 reduction, the latter providing fluoride for C(sp3)–F bond formation. The photochemical protocol efficiently converts electronrich substrates and tolerates a broad range of functional groups, whereas paired electrolysis extends the reaction to electronically deactivated substrates. Together, the two methods enable fluorination of diverse benzylic and aliphatic substrates, including late-stage fluorination of structurally complex derivatives of pharmaceuticals, natural products, and agrochemicals.
ER  -