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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 A Motornov, Athanasios Markos, P. Beier
Published 2018 · Chemistry, Medicine

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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.
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