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

HRID 591367Notes

Reaction equation

F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+]#N)=[CH:10][CH:9]=1>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:13]=[CH:12][C:11]([S:7]([F:19])([F:18])([F:17])([F:16])[F:6])=[CH:10][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

(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.

Workup

filtrationfiltered through a pad of SiO2 with the help of hexane
customRemoval of the solvent
customgave a colorless crystalline solid which
customwas purified by SiO2 column chromatography with hexane

Sources & evidence

ORD record: ord-0d7bde3b47784d40a9ac1ee53f09b078
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238660B1

Reaction notes

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