tetrakis(triphenylphosphine) palladium(0); formic acid in tetrahydrofuran 24 h; Heating;

benzene-selenenyl bromide; mercury dichloride; sodium nitrite in tetrahydrofuran; acetonitrile T=25°C; 4 h;

1: DMAP / diethyl ether / 4 h / 20 °C 2: 1.79 g / sodium borohydride / ethanol / 2 h / 20 °C 3: 90 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 22 h / 20 °C 4: DMAP / diethyl ether / 5 h / 20 °C 5: 0.23 g / DMAP / CH2Cl2 / 2 h / 20 °C 6: 58 percent / aq. HCl / 12 h / Heating View Scheme

1: DMAP / diethyl ether / 5 h / 20 °C 2: 0.23 g / DMAP / CH2Cl2 / 2 h / 20 °C 3: 58 percent / aq. HCl / 12 h / Heating View Scheme

1.1: ozone; Na2CO3 / CH2Cl2; methanol / -78 °C 1.2: 94 percent / Et3N; Ac2O / CH2Cl2 / 0 - 20 °C 2.1: 94 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C 3.1: DMAP / diethyl ether / 4 h / 20 °C 4.1: 1.79 g / sodium borohydride / ethanol / 2 h / 20 °C 5.1: 90 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 22 h / 20 °C 6.1: DMAP / diethyl ether / 5 h / 20 °C 7.1: 0.23 g / DMAP / CH2Cl2 / 2 h / 20 °C 8.1: 58 percent / aq. HCl / 12 h / Heating View Scheme

1: 94 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C 2: DMAP / diethyl ether / 4 h / 20 °C 3: 1.79 g / sodium borohydride / ethanol / 2 h / 20 °C 4: 90 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 22 h / 20 °C 5: DMAP / diethyl ether / 5 h / 20 °C 6: 0.23 g / DMAP / CH2Cl2 / 2 h / 20 °C 7: 58 percent / aq. HCl / 12 h / Heating View Scheme

1: 90 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 22 h / 20 °C 2: DMAP / diethyl ether / 5 h / 20 °C 3: 0.23 g / DMAP / CH2Cl2 / 2 h / 20 °C 4: 58 percent / aq. HCl / 12 h / Heating View Scheme

hydrogenchloride

1: 68 percent / AgNO2 / diethyl ether / 168 h / 20 °C 2: 81 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C 3: 86 percent / p-toluenesulfonic acid / 20 °C 4: 84 percent / Na2CO3 / benzene / 24 h / 80 - 90 °C 5: 95 percent / formic acid; Pd(PPh3)4 / tetrahydrofuran / 24 h / Heating View Scheme

1: 81 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C 2: 86 percent / p-toluenesulfonic acid / 20 °C 3: 84 percent / Na2CO3 / benzene / 24 h / 80 - 90 °C 4: 95 percent / formic acid; Pd(PPh3)4 / tetrahydrofuran / 24 h / Heating View Scheme