A rhodium-catalyzed transannulation of N-(per)fluoroalkyl-1,2,3-triazoles under microwave conditions - a general route to N-(per)fluoroalkyl-substituted five-membered heterocycles

Vladimir Motornov; Athanasios Markos; Petr Beier

doi:10.1039/c8cc01446a

A rhodium-catalyzed transannulation of N-(per)fluoroalkyl-1,2,3-triazoles under microwave conditions - a general route to N-(per)fluoroalkyl-substituted five-membered heterocycles

Chem Commun (Camb). 2018 Mar 27;54(26):3258-3261. doi: 10.1039/c8cc01446a.

Authors

Vladimir Motornov¹, Athanasios Markos², Petr Beier³

Affiliations

¹ The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic. beier@uochb.cas.cz and Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Moscow, Russian Federation.
² The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic. beier@uochb.cas.cz and Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, CZ-128 43 Prague 2, Czech Republic.
³ The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic. beier@uochb.cas.cz.

PMID: 29537032
DOI: 10.1039/c8cc01446a

Abstract

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.