Yield:1492771-69-3 92.5%

Reaction Conditions:

Stage #1: 1-(4-bromophenyl)triphenylethene;(4-aminophenyl)boronic acidwith tetrabutylammomium bromide;potassium carbonate in tetrahydrofuran;water at 20; for 0.5 h;Inert atmosphere;
Stage #2: with tetrakis(triphenylphosphine) palladium⁽⁰⁾ in tetrahydrofuran;water at 80; for 24 h;Inert atmosphere;

Steps:

2.4. Synthesis of P₅NH₂

TPE-Br (2.50 g, 6.08 mmol) and 4-aminophenylboronic acid (1.65 g, 12 mmol) were dissolved in the pure THF (50 mL), then TBAB (0.01 g) and K₂CO₃ (2 M, aq. soln., 9 mL) were added. The mixture was stirred at room temperature for 0.5 h under argon gas followed by addition of the Pd(PPh₃)₄ catalyst and then heated to 80 °C for 24h. The reaction mixture was concentrated and purified by column chromatography on a silica gel column with CH₂Cl₂/n-hexane (1:1 by volume) as eluent to give light yellow crystalline powder P₅NH₂ (2.35 g, 92.5% yield). ¹H NMR (300 MHz, DMSO-d₆) δ(ppm): 5.14-5.24 (s, 2H); 6.54-6.62 (d, J=8.4 Hz, 2H); 6.88-7.36 (m, 21H). MS (EI) calcd for C₃₂H₂₅N 423, found 423. Anal. calcd for C₃₂H₂₅N: C 90.74, H 5.95, N 3.31; Found: C 90.71, H 5.92, N 3.35.

References:

Luo, Miao;Zhou, Xie;Chi, Zhenguo;Liu, Siwei;Zhang, Yi;Xu, Jiarui [Dyes and Pigments,2014,vol. 101,p. 74 - 84]