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

Autor: Day DP; São Carlos Institute of Chemistry, University of São Paulo, São Carlos, São Paulo CEP 13560-970, Brazil., Mora Vargas JA; São Carlos Institute of Chemistry, University of São Paulo, São Carlos, São Paulo CEP 13560-970, Brazil., Burtoloso ACB; São Carlos Institute of Chemistry, University of São Paulo, São Carlos, São Paulo CEP 13560-970, Brazil.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Sep 03; Vol. 86 (17), pp. 12427-12435. Date of Electronic Publication: 2021 Aug 23.
DOI: 10.1021/acs.joc.1c01441
Abstrakt: 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 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%.
Databáze: MEDLINE