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Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF3CN.

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A general and regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles has been achieved through photocycloaddition of sydnone with trifluoroacetonitrile. This method employed trifluoroacetaldehyde O-(aryl)oxime as the CF3CN precursor and tolerated various functional… Click to show full abstract

A general and regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles has been achieved through photocycloaddition of sydnone with trifluoroacetonitrile. This method employed trifluoroacetaldehyde O-(aryl)oxime as the CF3CN precursor and tolerated various functional groups to furnish 3-trifluoromethyl 1,2,4-triazole products in moderate to good yields. Mechanistic experiments revealed an energy transfer from photocatalyst 4-CzIPN to the sydnone substrates.

Keywords: synthesis trifluoromethyl; trifluoromethyl triazoles; photocycloaddition sydnone; regioselective synthesis; sydnone

Journal Title: Chemical communications
Year Published: 2022

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