1: CH2Cl2 / 12 h / 20 °C 2: H2 / Rh(acac)(CO)2; biphephos / tetrahydrofuran / 8 h / 65 °C / 3800 Torr 3: 10-camphorsulfonic acid / tetrahydrofuran / 9 h / 20 °C 4: 100 percent / H2 / palladium on carbon / ethanol / 12 h / 20 °C / 760 Torr 5: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 20 °C 6: 96 percent / sodium; naphthalene / tetrahydrofuran / 1 h / -78 °C 7: 87 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 18 h / 0 °C 8: 95 percent / trifluoroacetic acid; NaHCO3 / 2 h / 20 °C View Scheme