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Peer-reviewedCC BY 4.0Chemistry (Weinheim an Der Bergstrasse, Germany)

FLP Mediated Conversion of Difluorobenzylalkynes to Fluoroallenyl Oniums via an SN1’ Pathway

  • Max Coles1
  • Tianhong Wang1
  • Rubi McLennan1
  • Long Kit Kwan1
  • Bivas Mondal2
  • Chakyu Richard Chan2
  • Rowan D. Young1
  1. 1School of Chemistry and Molecular Biosciences University of Queensland Brisbane Australia
  2. 2Department of Chemistry National University of Singapore Singapore Singapore
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Abstract

Fluoroallenes represent an attractive class of synthons and are congeners to naturally occurring haloallenes, yet their preparation remains challenging. We report that frustrated Lewis pair (FLP) mediated selective monodefluorination of difluorobenzylalkynes generates geminal fluorobenzylalkyne onium salts as kinetic products, which subsequently isomerize into thermodynamically preferred fluoroallenyl onium salts through an SN1′pathway. The onium‐stabilized fluoroallenes can undergo further derivatization at both allenic and onium positions, providing modular access to new fluorocarbon architectures.

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Cite

BibTeXRIS
BibTeX
@article{coles2026mediated,
  title = {{FLP Mediated Conversion of Difluorobenzylalkynes to Fluoroallenyl Oniums via an SN1’ Pathway}},
  author = {Max Coles and Tianhong Wang and Rubi McLennan and Long Kit Kwan and Bivas Mondal and Chakyu Richard Chan and Rowan D. Young},
  journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
  year = {2026},
  month = jun,
  doi = {10.1002/chem.71213},
  url = {https://doi.org/10.1002/chem.71213},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - FLP Mediated Conversion of Difluorobenzylalkynes to Fluoroallenyl Oniums via an SN1’ Pathway
AU  - Max Coles
AU  - Tianhong Wang
AU  - Rubi McLennan
AU  - Long Kit Kwan
AU  - Bivas Mondal
AU  - Chakyu Richard Chan
AU  - Rowan D. Young
PY  - 2026
DA  - 2026/06/02
JO  - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO  - 10.1002/chem.71213
UR  - https://doi.org/10.1002/chem.71213
AB  - Fluoroallenes represent an attractive class of synthons and are congeners to naturally occurring haloallenes, yet their preparation remains challenging. We report that frustrated Lewis pair (FLP) mediated selective monodefluorination of difluorobenzylalkynes generates geminal fluorobenzylalkyne onium salts as kinetic products, which subsequently isomerize into thermodynamically preferred fluoroallenyl onium salts through an SN1′pathway. The onium‐stabilized fluoroallenes can undergo further derivatization at both allenic and onium positions, providing modular access to new fluorocarbon architectures.
SN  - 0947-6539
SN  - 1521-3765
ER  -