Organofluorine / Alfa Chemistry
N-Fluoropyridinium tetrafluoroborate

N-Fluoropyridinium tetrafluoroborate

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N-Fluoropyridinium tetrafluoroborate
Catalog OFC107264095-1
CAS 107264-09-5
Category Electrophilic Fluorination Agents
MDL Number MFCD00153176
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Chemical Data Health Safety
Molecular Weight 184.9
Melting Point 186-192°C
Hazards Corrosive/Harmful
Hazard Statements Causes severe skin burns and eye damage.|Harmful if swallowed.
Case Study

N-Fluoropyridinium Tetrafluoroborate for the Synthesis of Silacycles via Metal Hydrogen Atom Transfer and Radical-Polar Crossover Mechanism

Synthesis of silacycles via metal hydrogen atom transfer and radical-polar crossover mechanism Sugimura T, et al. Tetrahedron Letters, 2024, 151, 155313.

In this study, N-fluoropyridinium tetrafluoroborate (Me3NFPY·BF4) was employed as an oxidant for the synthesis of silacycles, utilizing a novel combination of metal hydride hydrogen atom transfer (MHAT) and radical-polar crossover (RPC) mechanisms. The synthesis began with the one-step condensation of allylic silanols, which were subsequently cyclized under mild catalytic conditions using cobalt as the catalyst. This approach efficiently produced five-, six-, and seven-membered silacycles, with a strong preference for six-membered rings.
The experimental method demonstrated the effectiveness of N-fluoropyridinium tetrafluoroborate in promoting the desired transformation, acting as a key oxidant to initiate the reaction. The reaction conditions were optimized to ensure high selectivity of the silacycles, with the cobalt catalyst playing a pivotal role in facilitating the cyclization under low-temperature conditions. Density functional theory (DFT) calculations were employed to provide insights into the reaction mechanism, revealing the role of ring strain in influencing product selectivity.

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