Jump to main content
Jump to site search


General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles

Author affiliations

Abstract

Rhodium-catalyzed transformation of N-fluoroalkyl-1,2,3-triazoles in the presence of tert-butyl carbamate or water provided an efficient route to 2-fluoroalkyl imidazoles and 2-fluoroalkyl oxazoles, respectively. The treatment of N-fluoroalkyl-1,2,3-triazoles with excess water gave fluoroalkylated ketamides which were cyclized in situ to 2-fluoroalkyl oxazoles or thiazoles. Trifluoromethyl- and other difluoroalkyl-substituted heterocycles were obtained by the present method. The mechanism of this cascade transformation involving carbene insertion, HF elimination and cyclization was proposed.

Graphical abstract: General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles

Back to tab navigation

Supplementary files

Publication details

The article was received on 06 Sep 2019, accepted on 02 Oct 2019 and first published on 09 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01104H
Org. Chem. Front., 2019, Advance Article

  •   Request permissions

    General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles

    V. Motornov, V. Košťál, A. Markos, D. Täffner and P. Beier, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01104H

Search articles by author

Spotlight

Advertisements