1610542-31-8Relevant articles and documents
Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes
Jana, Sampad,Adhikari, Sweta,Cox, Michael R.,Roy, Sudeshna
supporting information, p. 1871 - 1874 (2020/02/20)
α-Fluoroalkynes are elusive molecules due to their instability and inaccessibility. Here, we show that α-fluoronitroalkenes can serve as synthetic surrogates of α-fluoroalkynes in [3+2] cycloaddition reactions with organic azides facilitated by a catalytic amount of trifluoroacetic acid (TFA). This work provides the first regioselective method to access 4-fluoro-1,5-disubstituted-1,2,3-triazoles.
Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes - Functionalized Fluorinated Building Blocks for Organic Synthesis
Motornov, Vladimir A.,Muzalevskiy, Vasiliy M.,Tabolin, Andrey A.,Novikov, Roman A.,Nelyubina, Yulia V.,Nenajdenko, Valentine G.,Ioffe, Sema L.
, p. 5274 - 5284 (2017/05/24)
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.
