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PreprintCC BYChemRxiv

Three-Component Alkene Difunctionalization Enabled by Continuous-Flow Generation of the NCF3 Anion

  • Dmitrii Nagornîi1
  • Maria Teresa Tiberi1,2
  • Mattia Lepori1
  • Nikolaos Kaplaneris1,3,4
  • Tom Roberts5,6
  • Sebastian C. Cosgrove5,6
  • Luigi Vaccaro2
  • Timothy Noel1
6 affiliations
  1. 1Flow Chemistry Group, University of Amsterdam, Science Park 904, Amsterdam, Netherlands, 1098 XH
  2. 2Laboratory of Green S.O.C. - Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, Perugia, Italy, 06123
  3. 3Department of Chemistry
  4. 4University of Crete Voutes
  5. 5School of Engineering & Physical Sciences
  6. 6Keele University
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Abstract

Multicomponent alkene difunctionalization provides an efficient route to molecular complexity by forging multiple bonds in a single operation. Although radical-polar crossover chemistry has greatly expanded the scope of these transformations, the use of highly reactive fluorinated nucleophiles remains largely unexplored because of their limited accessibility and poor stability. Here, we report the first three-component alkene difunctionalization employing the NCF3 anion as the nucleophilic reaction partner. The key to this transformation is the on-demand generation of the NCF3 anion in continuous flow, followed by its direct merger with visible-light photoredox catalysis. This strategy enables the coupling of a diverse range of radical precursors with styrenes and the flow-generated NCF3 anion through the sequential combination of radical and polar reactivities under mild photochemical conditions. The protocol accommodates extensive variation of the radical precursor, the alkene component and the NCF3 anion itself, and is applicable to the late-stage diversification of pharmaceuticals and agrochemicals. More broadly, this work demonstrates how continuous-flow generation of reactive intermediates can unlock multicomponent reaction manifolds that remain inaccessible using conventional batch methods.

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Cite

BibTeXRIS
BibTeX
@misc{nagornii2026threecomponent,
  title = {{Three-Component Alkene Difunctionalization Enabled by Continuous-Flow Generation of the NCF3 Anion}},
  author = {Dmitrii Nagornîi and Maria Teresa Tiberi and Mattia Lepori and Nikolaos Kaplaneris and Tom Roberts and Sebastian C. Cosgrove and Luigi Vaccaro and Timothy Noel},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008971/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008971/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Three-Component Alkene Difunctionalization Enabled by Continuous-Flow Generation of the NCF3 Anion
AU  - Dmitrii Nagornîi
AU  - Maria Teresa Tiberi
AU  - Mattia Lepori
AU  - Nikolaos Kaplaneris
AU  - Tom Roberts
AU  - Sebastian C. Cosgrove
AU  - Luigi Vaccaro
AU  - Timothy Noel
PY  - 2026
DA  - 2026/09/17
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008971/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008971/v1
AB  - Multicomponent alkene difunctionalization provides an efficient route to molecular complexity by forging multiple bonds in a single operation. Although radical-polar crossover chemistry has greatly expanded the scope of these transformations, the use of highly reactive fluorinated nucleophiles remains largely unexplored because of their limited accessibility and poor stability. Here, we report the first three-component alkene difunctionalization employing the NCF3 anion as the nucleophilic reaction partner. The key to this transformation is the on-demand generation of the NCF3 anion in continuous flow, followed by its direct merger with visible-light photoredox catalysis. This strategy enables the coupling of a diverse range of radical precursors with styrenes and the flow-generated NCF3 anion through the sequential combination of radical and polar reactivities under mild photochemical conditions. The protocol accommodates extensive variation of the radical precursor, the alkene component and the NCF3 anion itself, and is applicable to the late-stage diversification of pharmaceuticals and agrochemicals. More broadly, this work demonstrates how continuous-flow generation of reactive intermediates can unlock multicomponent reaction manifolds that remain inaccessible using conventional batch methods.
ER  -