A rhodium-catalyzed transannulation via ring-opening of N-(per)fluoroalkyl-substituted 1,2,3-triazoles followed by cycloaddition with different nitriles, enol ethers, isocyanates and silyl ketene acetals under microwave heating provided a highly efficient route to previously unreported N-(per)fluoroalkyl-substituted imidazoles, pyrroles, imidazolones and pyrrolones, respectively. These reactions were found to be applicable to the synthesis of a variety of 5-membered heterocycles bearing different (per)fluoroalkyl substituents as well as both electron-donating and electron-withdrawing groups attached to the heterocyclic core.

The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám 2 CZ 166 10 Prague 6 Czech Republic

The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám 2 CZ 166 10 Prague 6 Czech Republic and Department of Organic Chemistry Faculty of Science Charles University Hlavova 2030 8 CZ 128 43 Prague 2 Czech Republic

The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám 2 CZ 166 10 Prague 6 Czech Republic and Higher Chemical College D 1 Mendeleev University of Chemical Technology of Russia Miusskaya sq 9 125047 Moscow Russian Federation

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