To a screw-capped tube in N2 were added 5-(triazinyloxy)oxazole 3aa (100 mg, 0.318 mmol), 4-ethoxycarbonylphenylboronic acid (4b, 246 mg, 1.27 mmol), NiCl2 (dppf) (10.9 mg, 0.0159 mmol), K3PO4 (473 mg, 2.23), LiCl ( 40.4 mg, 0.954 mmol), DPPF (8.8 mg, 0.0159 mmol) and toluene (2.3 mL). The mixture was then stirred at 110 C for 6 h. The reaction mixture was cooled to room temperature. The reaction mixture was diluted, CH2Cl2 (10 mL) was filtered through a short diatomaceous earth pad and the filtrate was concentrated under reduced pressure. This purified the residue by fast column chromatography (EtOAc: hexane = 10:90) to give 1,4-bis[2-(4-methyl-5-phenyloxazole)]benzene 5aab (62.5 mg, 64%) as a white solid.
