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Peer-reviewedCC BY-NC 4.0Angewandte Chemie International Edition

Difluoromethylenation of Alkynes: Streamlined Access to Allyl Difluorides

  • Fabien Naullet
  • Sourav Mondal
  • Frédéric Guégan
  • Bastien Michelet
  • Sébastien Thibaudeau
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Abstract

A direct difluoromethylenation of alkynes has been developed using HF/pyridine as a dual acidic and fluorinating medium. The reaction proceeds via in situ generation of a primary oxocarbenium ion from formaldehyde, enabling efficient formation of two C(sp 3 )─F bonds and one C(sp 2 )═C(sp 2 ) bond in a single step without the need for pre‐functionalized reagents. This strategy offers a concise route to allyl difluorides as a complementary approach to incorporate difluoromethylene motifs into complex molecular frameworks. Additional spectroscopic and computational investigations provide insights into this mechanism.

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Cite

BibTeXRIS
BibTeX
@article{naullet2026difluoromethylenation,
  title = {{Difluoromethylenation of Alkynes: Streamlined Access to Allyl Difluorides}},
  author = {Fabien Naullet and Sourav Mondal and Frédéric Guégan and Bastien Michelet and Sébastien Thibaudeau},
  journal = {Angewandte Chemie International Edition},
  year = {2026},
  month = sep,
  doi = {10.1002/anie.8050538},
  url = {https://hal.science/hal-05773070v1},
  note = {CC BY-NC 4.0},
}
RIS
TY  - JOUR
TI  - Difluoromethylenation of Alkynes: Streamlined Access to Allyl Difluorides
AU  - Fabien Naullet
AU  - Sourav Mondal
AU  - Frédéric Guégan
AU  - Bastien Michelet
AU  - Sébastien Thibaudeau
PY  - 2026
DA  - 2026/09/30
JO  - Angewandte Chemie International Edition
DO  - 10.1002/anie.8050538
UR  - https://hal.science/hal-05773070v1
AB  - A direct difluoromethylenation of alkynes has been developed using HF/pyridine as a dual acidic and fluorinating medium. The reaction proceeds via in situ generation of a primary oxocarbenium ion from formaldehyde, enabling efficient formation of two C(sp 3 )─F bonds and one C(sp 2 )═C(sp 2 ) bond in a single step without the need for pre‐functionalized reagents. This strategy offers a concise route to allyl difluorides as a complementary approach to incorporate difluoromethylene motifs into complex molecular frameworks. Additional spectroscopic and computational investigations provide insights into this mechanism.
SN  - 1433-7851
SN  - 1521-3773
ER  -