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Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents

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Vitalij Vladimirovich Levin 1
Vitalij Vladimirovich Levin
10.1016/j.mencom.2015.07.001
Published 2015-07-08
Focus article , Volume 25, Issue 4, 239-244
36
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Dilman A. D., Levin V. V. Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 239-244.
GOST all authors (up to 50) Copy
Dilman A. D., Levin V. V. Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 239-244.
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TY - JOUR
DO - 10.1016/j.mencom.2015.07.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.001
TI - Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents
T2 - Mendeleev Communications
AU - Dilman, Alexander Davidovich
AU - Levin, Vitalij Vladimirovich
PY - 2015
DA - 2015/07/08
PB - Mendeleev Communications
SP - 239-244
IS - 4
VL - 25
ER -
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@article{2015_Dilman,
author = {Alexander Davidovich Dilman and Vitalij Vladimirovich Levin},
title = {Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.001},
number = {4},
pages = {239--244},
doi = {10.1016/j.mencom.2015.07.001}
}
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Dilman, Alexander Davidovich, and Vitalij Vladimirovich Levin. “Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents.” Mendeleev Communications, vol. 25, no. 4, Jul. 2015, pp. 239-244. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.001.
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Abstract

α-Fluorinated organosilanes Me3SiCF2X serve as versatile reagents for the synthesis of organofluorine compounds. Most reactions start from Lewis base activation of carbon–silicon bond through the intermediacy of five-coordinate siliconate species. Interaction of these silanes with suitable electrophiles leads to products of nucleophilic fluoroalkylation; an alternative pathway involves generation of difluorocarbene. These reagents can also be considered as equivalents of difluoromethylene radical anion and bis(carbanion) when carbon–heteroatom bond C–X is activated.

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