Metal- and Azide-Free Iodine-Promoted Aerobic Oxidative Cyclization to Trifluoromethylated Triazoles

J Org Chem. 2025 Jan 15. doi: 10.1021/acs.joc.4c02312. Online ahead of print.

Abstract

A novel metal- and azide-free methodology for the synthesis of trifluoromethylated 1,2,3-triazoles from arylamines with a new 3-bromo-1,1,1-trifluoropropan-2-one derived tosylhydrazone has been developed under mild reaction conditions. The new α-bromo-trifluoromethylated tosylhydrazone reagent was operationally safe and bench-stable from low-cost and readily commercially available starting materials in the iodine-promoted aerobic oxidative cycloaddition reaction with arylamines, affording a variety of trifluoromethylated 1,2,3-triazoles in good to excellent yields.