Isolable C‐Phosphonio‐Boratavinyl Anion

Abstract

A persistent C-phosphonio boratavinyl anion 1 has been successfully synthesized. This boron-containing vinyl-lithium 1, featuring a vinyl carbon with a negative charge (-1.59), considerably higher than that of carbon analogue 7 (-0.76), exhibits strongly nucleophilic and basic properties, as demonstrated by the results of rapid reactions with H 2 (10 bar, 15 min or 1 bar, 2 h at RT) and C 6 F 6 (1 equiv., 15 min at -80 • C). The reactions of boratavinyl anion 1 with electrophiles offer a convenient route for the introduction of a borata-alkene-based bulky and σ,π-double-donating substituent, enabling to efficiently stabilize reactive intermediates such as halogenogermylenes. Furthermore, the reaction with CO 2 takes place at the borata-alkene moiety, rather than at the P-ylide function, resulting in the double insertion of CO 2 into the B─C bond to afford a unique cyclic P-ylide 13.

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BibTeX RIS

BibTeX

@article{xu2026isolable,
  title = {{Isolable C‐Phosphonio‐Boratavinyl Anion}},
  author = {Huihui Xu and Aurora Rodríguez‐álvarez and Md Jabed Hossain and Antoine Baceiredo and Eddy Maerten and Nathalie Saffon‐merceron and Vicenç Branchadell and Tsuyoshi Kato},
  journal = {Angewandte Chemie International Edition},
  year = {2026},
  month = jul,
  doi = {10.1002/anie.2724882},
  url = {https://hal.science/hal-05768598v1},
  note = {CC BY-NC-ND 4.0},
}

RIS

TY  - JOUR
TI  - Isolable C‐Phosphonio‐Boratavinyl Anion
AU  - Huihui Xu
AU  - Aurora Rodríguez‐álvarez
AU  - Md Jabed Hossain
AU  - Antoine Baceiredo
AU  - Eddy Maerten
AU  - Nathalie Saffon‐merceron
AU  - Vicenç Branchadell
AU  - Tsuyoshi Kato
PY  - 2026
DA  - 2026/07/28
JO  - Angewandte Chemie International Edition
DO  - 10.1002/anie.2724882
UR  - https://hal.science/hal-05768598v1
AB  - A persistent C-phosphonio boratavinyl anion 1 has been successfully synthesized. This boron-containing vinyl-lithium 1, featuring a vinyl carbon with a negative charge (-1.59), considerably higher than that of carbon analogue 7 (-0.76), exhibits strongly nucleophilic and basic properties, as demonstrated by the results of rapid reactions with H 2 (10 bar, 15 min or 1 bar, 2 h at RT) and C 6 F 6 (1 equiv., 15 min at -80 • C). The reactions of boratavinyl anion 1 with electrophiles offer a convenient route for the introduction of a borata-alkene-based bulky and σ,π-double-donating substituent, enabling to efficiently stabilize reactive intermediates such as halogenogermylenes. Furthermore, the reaction with CO 2 takes place at the borata-alkene moiety, rather than at the P-ylide function, resulting in the double insertion of CO 2 into the B─C bond to afford a unique cyclic P-ylide 13.
SN  - 1433-7851
SN  - 1521-3773
ER  -

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