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 alpha-fluoro-alpha-triazol-1-yl ketones from sulfoxonium ylides via aazido-alpha-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N-3(-), 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%.

Automated summary

The work presents a new method to access alpha-fluoro-alpha-triazol-1-yl ketones from sulfoxonium ylides via aazido-alpha-fluoro ketone intermediates. This approach allows modification to both reactants and has been demonstrated with 15 examples, yielding between 22% to 75%.