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PreprintCC BYChemRxiv

HFO-1234yf as a Source of the 3,3-Difluoropropynyl Group

  • Georgina Rai1
  • Sarah Brock1
  • Zachary Bub1
  • Benedek Stadler1
  • Mark Crimmin
  1. 1Molecular Sciences Research Hub, Imperial College London, 82 Wood Lane, London, UK, W12 0BZ
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Abstract

Dimethyl(phenyl)(2,3,3-trifluoroallyl)silane, the defluorosilylation product of HFO-1234yf, reacts with KHMDS to form 3,3-difluoro-1-dimethyl(phenyl)silylpropyne. The mechanism of this transformation was rationalized through DFT calculations. Deprotonation and subsequent β-fluoride elimination leads to an allene intermediate. A base-catalyzed 1,3-proton migration from the allene then results in the difluoromethylated alkyne product. This alkynyl silane can undergo transmetalation with NHC-ligated Group 11 transition metal chloride complexes to form novel metal acetylide compounds with a 3,3-difluoropropynyl motif.

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Cite

BibTeXRIS
BibTeX
@misc{rai2026hfo1234yf,
  title = {{HFO-1234yf as a Source of the 3,3-Difluoropropynyl Group}},
  author = {Georgina Rai and Sarah Brock and Zachary Bub and Benedek Stadler and Mark Crimmin},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010606/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010606/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - HFO-1234yf as a Source of the 3,3-Difluoropropynyl Group
AU  - Georgina Rai
AU  - Sarah Brock
AU  - Zachary Bub
AU  - Benedek Stadler
AU  - Mark Crimmin
PY  - 2026
DA  - 2026/10/16
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010606/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010606/v1
AB  - Dimethyl(phenyl)(2,3,3-trifluoroallyl)silane, the defluorosilylation product of HFO-1234yf, reacts with KHMDS to form 3,3-difluoro-1-dimethyl(phenyl)silylpropyne. The mechanism of this transformation was rationalized through DFT calculations. Deprotonation and subsequent β-fluoride elimination leads to an allene intermediate. A base-catalyzed 1,3-proton migration from the allene then results in the difluoromethylated alkyne product. This alkynyl silane can undergo transmetalation with NHC-ligated Group 11 transition metal chloride complexes to form novel metal acetylide compounds with a 3,3-difluoropropynyl motif.
ER  -