Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach.

The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N3-, followed by a subsequent CuAAC reaction with arylacetylenes to install a 1,4-triazolo moiety. The approach allows for modification to both the sulfoxonium ylide and arylacetylene reactants. Fifteen examples have been reported, with yields ranging between 22% and 75%.

Citation

David Philip Day, Jorge Andrés Mora Vargas, Antonio Carlos Bender Burtoloso. Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach. The Journal of organic chemistry. 2021 Sep 03;86(17):12427-12435

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PMID: 34424699

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