Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis
Publication type: Journal Article
Publication date: 2017-05-10
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28448146
Organic Chemistry
Abstract
A new highly efficient method for the synthesis of 2-fluoro-2-nitrostyrenes was described. Radical nitration of readily available 2-bromo-2-fluorostyrenes with Fe(NO3)3·9H2O resulted in the formation of the corresponding α-fluoro-nitroalkenes in isolated yields up to 92%. The reaction proceeded as a nitration-debromination sequence to highly stereoselectively give α-fluoro-nitroalkenes as Z-isomers only. The broad scope of this method was demonstrated. Prepared monofluorinated alkenes were shown to be versatile building blocks for the synthesis of various fluorinated products.
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65
Total citations:
65
Citations from 2024:
20
(30.77%)
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GOST
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Motornov V. A. et al. Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis // Journal of Organic Chemistry. 2017. Vol. 82. No. 10. pp. 5274-5284.
GOST all authors (up to 50)
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Motornov V. A., Muzalevskiy V. M., Tabolin A. A., Novikov R. G., Nelyubina Y. V., Nenajdenko V. G., Ioffe S. L. Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis // Journal of Organic Chemistry. 2017. Vol. 82. No. 10. pp. 5274-5284.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.7b00578
UR - https://doi.org/10.1021/acs.joc.7b00578
TI - Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis
T2 - Journal of Organic Chemistry
AU - Motornov, Vladimir A
AU - Muzalevskiy, Vasily M.
AU - Tabolin, Andrey A
AU - Novikov, Roman G.
AU - Nelyubina, Yulia V.
AU - Nenajdenko, Valentine G.
AU - Ioffe, Sema L.
PY - 2017
DA - 2017/05/10
PB - American Chemical Society (ACS)
SP - 5274-5284
IS - 10
VL - 82
PMID - 28448146
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Motornov,
author = {Vladimir A Motornov and Vasily M. Muzalevskiy and Andrey A Tabolin and Roman G. Novikov and Yulia V. Nelyubina and Valentine G. Nenajdenko and Sema L. Ioffe},
title = {Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.joc.7b00578},
number = {10},
pages = {5274--5284},
doi = {10.1021/acs.joc.7b00578}
}
Cite this
MLA
Copy
Motornov, Vladimir A., et al. “Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis.” Journal of Organic Chemistry, vol. 82, no. 10, May. 2017, pp. 5274-5284. https://doi.org/10.1021/acs.joc.7b00578.
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