Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis

Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2017, Volume: 82, Number: 10, Pages: 5274-5284 Pages count : 11 DOI: 10.1021/acs.joc.7b00578

Authors

Motornov Vladimir A. ^1,2 , Muzalevskiy Vasiliy M. ³ , Tabolin Andrey A. ² , Novikov Roman A. ^2,4 , Nelyubina Yulia V. ⁵ , Nenajdenko Valentine G. ³ , Ioffe Sema L. ²

Affiliations

1	Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow 125047, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation
3	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119992, Russian Federation
4	V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, Moscow 119991, Russian Federation
5	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow 119991, Russian Federation

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.

Motornov V.A. , Muzalevskiy V.M. , Tabolin A.A. , Novikov R.A. , 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. V.82. N10. P.5274-5284. DOI: 10.1021/acs.joc.7b00578 WOS Scopus OpenAlex

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