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

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 k...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2019-11, Vol.6 (22), p.3776-3780
Main Authors: Motornov, Vladimir, Košťál, Vojtěch, Markos, Athanasios, Täffner, Dominik, Beier, Petr
Format: Article
Language:English
Subjects:
Azoles
Catalysis
Chemical reactions
Excess water
Heterocyclic compounds
Organic chemistry
Oxazoles
Rhodium
Ring opening
Thiazoles
Triazoles
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo01104h