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- W3186259095 abstract "A facile, scalable synthesis of previously inaccessible trifluoromethyl and perfluoroalkyl triazoles is disclosed. Mediated by copper, this catalytic protocol enables access to 4-perfluoroalkyl triazoles from commodity chemicals. A catalytic Cu(II) system wherein copper serves two roles (generation of N-tosyl-2-vinyldiazenes and N–N bond formation) allows for rapid assembly of 5-carboxyl-4-perfluoroalkyl-triazoles from N-tosylhydrazide and perfluoroalkyl acetoacetates. Ethyl 4,4,4-trifluoro-3-(2-tosylhydrazineylidene)butanoate, a previously unknown air and bench stable reagent for access to CF3-triazoles, was developed to enable this chemistry. This led to the identification of a series of crystalline hydrazone reagents that could be used as templates to construct an array of triazoles. Hydrolysis and decarboxylation parlay this approach into a means to access 5-H-4-CF3-triazoles. The approach exhibits high functional group tolerance and can be executed on a multigram scale." @default.
- W3186259095 created "2021-08-02" @default.
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- W3186259095 date "2021-07-21" @default.
- W3186259095 modified "2023-09-25" @default.
- W3186259095 title "Copper-Catalyzed Synthesis of 5-Carboxyl-4-perfluoroalkyl Triazoles" @default.
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- W3186259095 doi "https://doi.org/10.1021/acs.orglett.1c02037" @default.
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