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Issue 22, 2019
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General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles

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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

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Article information


Submitted
06 Sep 2019
Accepted
02 Oct 2019
First published
09 Oct 2019

Org. Chem. Front., 2019,6, 3776-3780
Article type
Research Article

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, 6, 3776
DOI: 10.1039/C9QO01104H

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