4-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate → 1,4-Bis(pentafluorosulfanyl)biphenyl

Participants

Reaction Conditions

Reaction Steps

(Kirsch, et al., Angew. Chem. 1999, 111, 2174; Kirsch, et al., Angew. Chem. Int. Ed. 1999, 38, 1989-1992) Palladium(II) acetate (0.3 mg, 0.001 mmol) was added to a solution of 1 (14.5 mg, 0.0384 mmol) in 0.15 g of methanol. The reaction mixture was stirred at 70° C. for 5.5 h and filtered through a pad of SiO2 with the help of hexane. Removal of the solvent gave a colorless crystalline solid which was purified by SiO2 column chromatography with hexane to give 14 (7.7 mg) as colorless crystals (99%); m.p. 196.0-197.0° C. (in sealed tube). IR (ATR): {tilde over (v)}=3007, 2992, 1599, 1481, 1391, 1277, 1260, 1101, 831, 810 cm−1. MS (GC, EI): m/z=406 [M+], 387 [M+-F], 282, 190. 1H NMR (500 MHz, CDCl3): δ=7.87 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.6 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ=153.7 (C), 142.3 (C), 127.6 (2CH), 126.7 (2CH) ppm. 19F NMR (470 MHz, CDCl3): δ=84.0 (quint, J=150 Hz, 1 F), 63.0 (d, J=150 Hz, 4 F) ppm.

Provenance & Evidence