“…HCl (5.72 mL, 57.2 mmol) was added dropwise at 0 8C. Then, the reaction mixture was warmed to rt and stirred for 24 h. After this period, the solvent was concentrated in vacuum and the crude reaction mixture was basified with ammonia to pH 8, then extracted with ethyl acetate, and the organic layer was dried over 1, 140.9, 140.5, 139.2, 135.0, 134.7, 133.8, 132.8, 132.5, 132.1, 131.9, 130.2, 129.1, 128.7, 123.5, 114.8, 22.3, 20.1, 19.9, 19.8 2',2''', 5',4,5,3,2-dioxaborolan-2-yl)-[1,1':4',1'':4'',1'''-quaterphenyl]-4-amine ( 15).F ollowing the procedure outlined for 8,c ompound 14 (805 mg, 1.76 mmol), bis(pinacolato)diboron (508 mg, 2.0 mmol), Pd(dppf) 2 Cl 2 (219 mg, 0.36 mmol), and KOAc (530 mg, 5.41 mmol) in anhydrous DME (26 mL) 2, 144.1, 142.3, 140.8, 140.3, 140.2, 140.0, 138.1, 132.7, 132.0, 131.9, 131.6, 131.5, 130.2, 128.9, 128.7, 114.8, 83.5, 24.9, 21.7, 20.1, 20.0, 19.8 4 (77 mg, 0.07 mmol), AgCO 3 (827 mg, 3.0 mmol), and anhydrous THF (40 mL) as the solvent. The mixture was stirred at rt for 12 h. Column chromatography (SiO 2 ;c yclohexane/EtOAc, 1:1) gave compound 16 as ay ellowish syrup (200 mg 3, 143.2, 140.9, 140.8, 140.6, 140.4, 140.1, 140.0, 136.4, 136.3, 132.8, 132.7, 132.6, 132.1, 132.0, 132.0, 131.3, 130.2, 129.1, 128.9, 114.9, 107.7, 60.5, 20.1, 20.0, 0.1 ppm.…”