One-Pot Telescoping <i>S</i>‑Transfer\nand Trifluoromethylation for the Synthesis of 2‑CF<sub>3</sub>S‑Imidazoles with <i>N</i>‑Oxides as Convenient\nPrecursors

Readily available\n2-unsubstituted imidazole <i>N</i>-oxides\nwere examined as starting materials for the preparation of fully substituted\n1,4,5-aryl/alkyl 2-trifluoromethylsulfanyl-imidazoles. Whereas activation\nof the <i>N</i>-oxide function followed by attempted nucleophilic\naddition of the <sup>–</sup>SCF<sub>3</sub> was in vain, the\nalternative approach involving “sulfur transfer reaction”\nand subsequent electrophilic trifluoromethylation with Togni reagent\nprovided target products in high yield via a one-pot procedure. The\nstructure of representative enantiomerically pure imidazol-2-yl trifluoromethyl\nsulfide was confirmed by X-ray analysis.