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