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To a solution of tetra(n-butyl)ammonium hydroxide (TBAOH, 19.0mL; 1.0M; 19 mol) in methanol were added toluene (30 mL, 4-(N,N′-ditolylamino)-1- bromobenzene (4.00 g, 11.4 mmol, 2,2′-biphenyldiboronic acid, 1.50 g, 6.20 mmol, and tetrakis(triphenylphosphine)palladium(0, Pd(PPh 3)4, 34 mg, 0.029 mmol, The mixture was refluxed with stirring under N2 for 48 h. The solvent was removed on a rotary evaporator and the residue was dissolved in chloroform. The solution was washed with 5% HCl and brine, dried over anhydrous MgSO4, and filtered. The solvent was evaporated and purified by column chromatography on silica gel using a mixture of chloroform and hexanes (ratio, 1/3) as eluent. The yield was 0.93 g (22, 1HNMR (CDCl3, δ7.43-7.38 (m, 2H, 7.33-7.28 (m, 4H, 7.21-7.16 (m, 2H, 6.98-6.86 (m, 16H, 6.70-6.64 (d, 4H, 6.52-6.46 (d, 4H, 2.28-2.20 s, 12H
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3): δ7.43-7.38 (m, 2H), 7.33-7.28 (m, 4H), 7.21-7.16 (m, 2H), 6.98-6.86 (m, 16H), 6.70-6.64 (d, 4H), 6.52-6.46 (d, 4H), 2.28-2.20 (s, 12H).
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