3-Butyn-1-OL → 4-(Biphenyl-4-yl)but-3-yn-1-ol

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A sample of 4-iodobiphenyl (400 mg, 1.40 mmol) and (PPh3)4Pd (32 mg, 0.02 mmol) were dissolved in Et3N (6 mL) and stirred at 23° C. for 15 min before CuI (13.5 mg, 0.071 mmol) and but-3-yn-1-ol (0.129 mL, 1.71 mmol) were added. The reaction mixture was stirred at 23° C. for 3 h and then diluted with CH2Cl2, washed with saturated aqueous NH4Cl and saturated aqueous NaCl, and dried over Na2SO4. Evaporation in vacuo yielded the crude product. Flash chromatography (SiO2, 20% EtOAc-hexanes) afforded the title compound (270 mg, 85%) as a white solid: 1H NMR (CDCl3, 500 MHz) δ 7.59 (dd, 2H, J=8.5 Hz), 7.54 (dd, 4H, J=8.5 Hz), 7.44 (t, 2H, J=7.5 Hz), 7.36 (t, 1H, J=7.5 Hz), 3.84 (t, 2H, J=6.5 Hz), 2.73 (t, 2H, J=6.0 Hz); 13C NMR (CDCl3, 125 MHz) δ 140.6, 140.2, 132.0, 128.7, 127.5, 126.9, 126.8, 122.2, 87.0, 82.2, 61.1, 23.9.

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