Trimethylsilyl iodide → 4-Iodophenylsulfur Pentafluoride

Participants

Reaction Steps

(Bowden, et al., Tetrahedron 2000, 56, 3393-3408) Trimethylsilyl iodide (15.0 mg, 0.0750 mmol) was added to a solution of 1 (11.0 mg, 0.0346 mmol) in [BMIM][BF4] (67.6 mg). After stifling for 5 min the mixture was extracted with hexane (0.5 mL×3) and the combined extracts was evaporated to give pure 25b as a colorless oil (4.6 mg, 40%): MS (GC, EI): m/z=330 [M+], 311 [M+ F], 222, 96. 1H NMR (500 MHz, CDCl3): δ=7.82 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.8 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ=137.9 (2CH), 127.5 (2CH), 98.2 (C) ppm. 19F NMR (470 MHz, CDCl3): δ=83.5 (quint, J=151 Hz, 1 F), 62.8 (d, J=151 Hz, 4 F) ppm.

Provenance & Evidence