Triphenylphosphine → 2'-(pyridin-2-yl)-9H-2,9'-bicarbazole

Participants

Reaction Conditions

Reaction Steps

A solution of 9-(2′-nitrobiphenyl-4-yl)-2-(pyridin-2-yl)-9H-carbazole (1.00 g, 2.27 mmol, 1.0 eq) and PPh3 (2.38 g, 9.06 mmol, 4.0 eq) in 1,2-dichlorobenzene (15 mL) was stirred at refluxed temperature of 175-185° C. in an oil bath and for 46 hours under nitrogen, and cooled. The solvent was removed by distillation under high vacuum. The residue was purified through column chromatography on silica gel using hexane/ethyl acetate (10:1-5:1-3:1) as an eluent to obtain the desired product, 2′-(pyridin-2-yl)-9H-2,9′-bicarbazole, as a brown solid (814 g in 88% yield). 1H NMR (DMSO-d6, 400 MHz): δ 7.27 (t, J=8.0 Hz, 1H), 7.30-7.36 (m, 2H), 7.42 (dd, J=8.8, 1.2 Hz, 1H), 7.45-7.51 (m, 3H), 7.59 (d, J=8.8 Hz, 1H), 7.75 (d, J=1.6 Hz, 1H), 7.84-7.88 (m, 1H), 8.04 (d, J=8.4 Hz, 2H), 8.21 (s, 1H), 8.27 (d, J=8.0 Hz, 1H), 8.33 (d, J=7.2 Hz, 1H), 8.39 (d, J=7.6 Hz, 1H), 8.44 (d, J=8.8 Hz, 1H), 8.61 (d, J=4.8 Hz, 1H), 11.53 (s, 1H).

Provenance & Evidence