Mild C─F Activation of Azido(per)Fluoroalkanes
4 affiliations
- 1Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Prague Czechia
- 2V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry The National Academy of Sciences of Ukraine Kyiv Ukraine
- 3Department of Organic Chemistry Faculty of Sciences Charles University Prague Czechia
- 4Department of Physical Chemistry University of Chemistry and Technology Prague Czechia
Abstract
In this study, we explore a new approach for the mild and selective activation of C(sp3)–F bonds in fluorinated azidoalkanes. Our approach utilizes electrophilic azide groups, which promote fluoride elimination and enable nucleophilic addition to newly formed electrophilic sites. This method achieves rapid, high‐yield transformations of (per)fluoroalkyl azides into novel sulfur‐containing azides, imines, and triazoles under mild conditions and using inexpensive reagents. The reaction proceeds without metal catalysts or external energy input and displays broad functional group tolerance, including toward thiol‐sensitive motifs. Mechanistic studies supported by spectroscopy and x‐ray crystallography, corroborated by ab initio calculations, reveal key azide intermediates and establish the denitrogenation pathway via α,α‐disubstituted species. This transformation provides a practical and scalable route for the conversion of (per)fluoroalkyl azides into nitrogen‐ and sulfur‐functionalized scaffolds, advancing C─F activation processes.
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BibTeX
@article{shaitanova2026mild,
title = {{Mild C─F Activation of Azido(per)Fluoroalkanes}},
author = {Olena Shaitanova and María Martínez Mallo and Sergii Suikov and Blanka Klepetářová and Josef Filgas and Petr Slavíček and Lucie Bednárová and Petr Beier},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
year = {2026},
month = jul,
doi = {10.1002/chem.71323},
url = {https://doi.org/10.1002/chem.71323},
note = {CC BY-NC 4.0},
}
RIS
TY - JOUR
TI - Mild C─F Activation of Azido(per)Fluoroalkanes
AU - Olena Shaitanova
AU - María Martínez Mallo
AU - Sergii Suikov
AU - Blanka Klepetářová
AU - Josef Filgas
AU - Petr Slavíček
AU - Lucie Bednárová
AU - Petr Beier
PY - 2026
DA - 2026/07/09
JO - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO - 10.1002/chem.71323
UR - https://doi.org/10.1002/chem.71323
AB - In this study, we explore a new approach for the mild and selective activation of C(sp3)–F bonds in fluorinated azidoalkanes. Our approach utilizes electrophilic azide groups, which promote fluoride elimination and enable nucleophilic addition to newly formed electrophilic sites. This method achieves rapid, high‐yield transformations of (per)fluoroalkyl azides into novel sulfur‐containing azides, imines, and triazoles under mild conditions and using inexpensive reagents. The reaction proceeds without metal catalysts or external energy input and displays broad functional group tolerance, including toward thiol‐sensitive motifs. Mechanistic studies supported by spectroscopy and x‐ray crystallography, corroborated by ab initio calculations, reveal key azide intermediates and establish the denitrogenation pathway via α,α‐disubstituted species. This transformation provides a practical and scalable route for the conversion of (per)fluoroalkyl azides into nitrogen‐ and sulfur‐functionalized scaffolds, advancing C─F activation processes.
SN - 0947-6539
SN - 1521-3765
ER -