aluminium trichloride

potassium phosphate; Wilkinson's catalyst; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl in 1,4-dioxane T=80°C; 20 h; Inert atmosphere;

1: 77 percent / Et3N / tetrahydrofuran / 4 h / Heating 2: Na2CO3 / CH2Cl2 / 0.5 h 3: 8.36 g / EtONa / ethanol / 0.5 h / Heating 4: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 5: 79 percent / MeOH; NaH / toluene / 4 h / Heating 6: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 7: CAN / acetonitrile; H2O / 0.5 h / 20 °C 8: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 9: Cs2CO3 / o-xylene / 20 h / 130 °C 10: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

sulfuric acid T=80 - 140°C;

sulfuric acid T=140°C; 1.25 h;

1: 77 percent / Et3N / tetrahydrofuran / 4 h / Heating 2: Na2CO3 / CH2Cl2 / 0.5 h 3: 8.36 g / EtONa / ethanol / 0.5 h / Heating 4: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 5: 79 percent / MeOH; NaH / toluene / 4 h / Heating 6: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 7: CAN / acetonitrile; H2O / 0.5 h / 20 °C 8: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C View Scheme

1: 77 percent / Et3N / tetrahydrofuran / 4 h / Heating 2: Na2CO3 / CH2Cl2 / 0.5 h 3: 8.36 g / EtONa / ethanol / 0.5 h / Heating 4: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 5: 79 percent / MeOH; NaH / toluene / 4 h / Heating 6: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 7: CAN / acetonitrile; H2O / 0.5 h / 20 °C View Scheme

triethylamine in diethyl ether 3 h;

1: H2SO4 / 80 - 140 °C 2: LiAlH4 / diethyl ether / Heating View Scheme