General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles
Literature Information
Publication Date
2019-10-09
DOI
10.1039/C9QO01104H
Impact Factor
5.281
Authors
Vojtěch Košťál, Dominik Täffner, Petr Beier
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![trans-2-{[(Tert-butoxy)carbonyl]amino}cyclobutane-1-carboxylic acid structure](https://static.chemtradehub.com/structs/951/951173-25-4-27cd.webp "trans-2-{[(Tert-butoxy)carbonyl]amino}cyclobutane-1-carboxylic acid structure")
trans-2-{[(Tert-butoxy)carbonyl]amino}cyclobutane-1-carboxylic acid
CAS Number:
951173-25-4
Molecular Formula:
C10H17NO4
Methyl 2-amino-4-(4-chlorophenyl)-5-pyrimidinecarboxylate
CAS Number:
1133115-56-6
Molecular Formula:
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