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Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes

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Abstract

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.

Graphical abstract: Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes

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Article information


Submitted
27 Nov 2019
Accepted
03 Jan 2020
First published
04 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes

S. Jana, S. Adhikari, M. R. Cox and S. Roy, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09216A

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