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Peer-reviewedCC BY-NC 3.0Chemical Science

A sulfinate–azide hybrid reagent for sequential radical fluoroalkylation and click reaction†

  • Pallavi Halkarni1,2
  • Mykyta Ziabko1,2
  • Veronika Vrábelová1
  • Marek Opelka1
  • Yu Qianfei3
  • Xihe Bi3
  • Sergeii Suikov1
  • Petr Pospíšil1,4
  • Tomáš David1
  • Soňa Boháčová1
  • Blanka Klepetářová1
  • Petr Beier1
4 affiliations
  1. 1Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nam. 2 160 00 Prague Czechia
  2. 2Department of Chemistry, Faculty of Science, Charles University Hlavova 2030/8 128 43 Prague Czechia
  3. 3Department of Chemistry, Northeast Normal University 5286 Renmin Street Changchun 130024 China
  4. 4Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice Studentská 573 532 10 Pardubice Czechia
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Abstract

A new clickable radical fluoroalkylating reagent, sodium 2-azido-1,1,2,2-tetrafluoroethanesulfinate, was prepared in one step from tetrafluoroethylene, sodium azide and sulfur dioxide. Oxidant-induced radical fluoroalkylation of arenes, heteroarenes, alkenes, and thiols, using this reagent, afforded azidotetrafluoroalkylated adducts. Their subsequent click reactions with alkynes led to N-fluoroalkylated triazoles. The synthetic sequence demonstrated the use of the new reagent as a clickable azidotetrafluoroethyl radical synthon, enabling connection to a diverse array of moieties, including a monoclonal antibody, via a triazole linker.

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Cite

BibTeXRIS
BibTeX
@article{halkarni2026sulfinateazide,
  title = {{A sulfinate–azide hybrid reagent for sequential radical fluoroalkylation and click reaction†}},
  author = {Pallavi Halkarni and Mykyta Ziabko and Veronika Vrábelová and Marek Opelka and Yu Qianfei and Xihe Bi and Sergeii Suikov and Petr Pospíšil and Tomáš David and Soňa Boháčová and Blanka Klepetářová and Petr Beier},
  journal = {Chemical Science},
  year = {2026},
  month = sep,
  doi = {10.1039/d6sc06249k},
  url = {https://doi.org/10.1039/d6sc06249k},
  note = {CC BY-NC 3.0},
}
RIS
TY  - JOUR
TI  - A sulfinate–azide hybrid reagent for sequential radical fluoroalkylation and click reaction†
AU  - Pallavi Halkarni
AU  - Mykyta Ziabko
AU  - Veronika Vrábelová
AU  - Marek Opelka
AU  - Yu Qianfei
AU  - Xihe Bi
AU  - Sergeii Suikov
AU  - Petr Pospíšil
AU  - Tomáš David
AU  - Soňa Boháčová
AU  - Blanka Klepetářová
AU  - Petr Beier
PY  - 2026
DA  - 2026/09/15
JO  - Chemical Science
DO  - 10.1039/d6sc06249k
UR  - https://doi.org/10.1039/d6sc06249k
AB  - A new clickable radical fluoroalkylating reagent, sodium 2-azido-1,1,2,2-tetrafluoroethanesulfinate, was prepared in one step from tetrafluoroethylene, sodium azide and sulfur dioxide. Oxidant-induced radical fluoroalkylation of arenes, heteroarenes, alkenes, and thiols, using this reagent, afforded azidotetrafluoroalkylated adducts. Their subsequent click reactions with alkynes led to N-fluoroalkylated triazoles. The synthetic sequence demonstrated the use of the new reagent as a clickable azidotetrafluoroethyl radical synthon, enabling connection to a diverse array of moieties, including a monoclonal antibody, via a triazole linker.
SN  - 2041-6520
SN  - 2041-6539
ER  -