An oven-dried three-necked round bottom flask and stir bar was equipped with three septa and purged with dry nitrogen gas for 30 minutes. Anhydrous toluene (5.6 mL, 0.18 M), 4,7-dibromobenzo[c]-1,2,5-thiadiazole (293.9 mg, 1.00 mmol, 1 eq.), DPPF (27.7 mg, 0.05 mmol), palladium (II) acetate (16.8 mg, 0.075 mmol), and sodium tert-butoxide (211.4 mg, 2.20 mmol, 2.2 eq.) were added to the flask. Benzophenone imine (0.34 mL, 2.00 mmol, 2 eq.) was added dropwise by syringe under nitrogen. The solution was heated to 90°C for 24 hours. On workup, the solution was diluted with water, and washed with ethyl acetate. The water layer was washed with dichloromethane. The organic layers were combined, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to yield a thick, dark red oil. The oil was taken up in hot hexanes and cooled to room temperature and filtered to yield a brick-red powder (326.8 mg, 0.66 mmol, 66% yield).

¹H NMR (400 MHz, CDCl₃) δ 7.820 (d, J = 8 Hz, 4H), 7.491 (m, 2H), 7.411 (m, 4H), 7.209 (m, 2H), 7.129 (m, 4H), 7.057 (d, J = 8 Hz, 4H), 6.456 (s, 2H).

¹³C NMR (400 MHz, CDCl₃) δ 171.090, 149.635, 139.313, 138.911, 136.346, 131.132, 129.690, 128.680, 128.187, 127.792, 117.220.

Infrared Spectra

1607 cm^-1 (imine C=N), 1596 cm^-1, 1577 cm^-1 (BTD C=N)

High-Resolution Mass Spectrometry

Calculated: 494.1565 m/z

Found (M + 1)⁺: 495.1635 m/z