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. Issue 26 (14th March 2018)

• Record Type: Journal Article
• Authors: Motornov, Vladimir; Markos, Athanasios; Beier, Petr
• Is Part Of: Chemical communications. Volume 54:Issue 26(2018)
• Page Start: 3258
• Page End: 3261
• Publication Date: 2018-03-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc01446a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An efficient rhodium-catalyzed microwave-assisted transannulation of N -(per)fluoroalkyl-1, 2, 3-triazoles to previously inaccessible N -(per)fluoroalkyl five-membered heterocycles was developed. 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.