Cesium carbonate → HCID 86714199, compound

Participants

Reaction Steps

A solution of 4,4,5,5-Tetramethyl-2-[(1E)-2-(phenylethenyl]-1,3,2-dioxaborolane (15, 1.62 g, 7.04 mmol), 2-iodonaphtho[2,3-b]thiophene (5, 1.04 g, 3.35 mmol), Cs2CO3 (6.53 g, 20.04 mmol), and Pd(PPh3)4 (154.5 mg, 0.134 mmol, 4% mol) in dry DMF (70 mL) was heated at 80° C. for overnight for 2 days. The reaction mixture was then allowed to cool to room temperature, the formed precipitate was filtered and washed with methanol, water, and hexanes to yield a green crude solid. The crude solid was purified by vacuum sublimation in high vacuum (Tsub=250° C.) to give PVNT as an off-white solid (480 mg, 50% yield). 1H NMR (500 MHz, C2D2Cl4) δ 8.24 (s, 1H), 8.15 (s, 1H), 7.96 (m, 1H), 7.89 (m, 1H), 7.45 (m, 5H), 7.34 (s, 1H), 7.32 (d, J=16.0 Hz, 1H), 7.21 (d, J=8.0 Hz, 2H), 6.98 (d, J=16 Hz, 1H). Anal. calcd. for (C20H14S): C, 83.88; H, 4.93. Found: C, 84.37; H, 4.74. m.p. 305-307° C.

Provenance & Evidence