1: 85 percent / acetone / 10 h / Heating 2: 75 percent / K2CO3 / acetonitrile / 10 h / Heating 3: 98 percent / H2 / Pd/CaCO3 / methanol / 1 h / 1810.02 Torr / Ambient temperature 4: 85 percent / PPh3, CCl4, K2CO3 / CH2Cl2 / 8 h / Heating 5: 1,4-dicyanonaphthalene, K2CO3 / propan-2-ol / 3 h / Ambient temperature; Irradiation 6: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) r.t., 1 h 7: NaBH4 / ethanol / 3 h / Heating View Scheme

1: 75 percent / K2CO3 / acetonitrile / 10 h / Heating 2: 98 percent / H2 / Pd/CaCO3 / methanol / 1 h / 1810.02 Torr / Ambient temperature 3: 85 percent / PPh3, CCl4, K2CO3 / CH2Cl2 / 8 h / Heating 4: 1,4-dicyanonaphthalene, K2CO3 / propan-2-ol / 3 h / Ambient temperature; Irradiation 5: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) r.t., 1 h 6: NaBH4 / ethanol / 3 h / Heating View Scheme

1: 75 percent / K2CO3 / acetonitrile / 10 h / Heating 2: 98 percent / H2 / Pd/CaCO3 / methanol / 1 h / 1810.02 Torr / Ambient temperature 3: 85 percent / PPh3, CCl4, K2CO3 / CH2Cl2 / 8 h / Heating 4: 1,4-dicyanonaphthalene, K2CO3 / propan-2-ol / 3 h / Ambient temperature; Irradiation 5: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) r.t., 1 h 6: NaBH4 / ethanol / 3 h / Heating View Scheme

1: 98 percent / H2 / Pd/CaCO3 / methanol / 1 h / 1810.02 Torr / Ambient temperature 2: 85 percent / PPh3, CCl4, K2CO3 / CH2Cl2 / 8 h / Heating 3: 1,4-dicyanonaphthalene, K2CO3 / propan-2-ol / 3 h / Ambient temperature; Irradiation 4: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) r.t., 1 h 5: NaBH4 / ethanol / 3 h / Heating View Scheme

1: 1,4-dicyanonaphthalene, K2CO3 / propan-2-ol / 3 h / Ambient temperature; Irradiation 2: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) r.t., 1 h 3: NaBH4 / ethanol / 3 h / Heating View Scheme

1: 85 percent / PPh3, CCl4, K2CO3 / CH2Cl2 / 8 h / Heating 2: 1,4-dicyanonaphthalene, K2CO3 / propan-2-ol / 3 h / Ambient temperature; Irradiation 3: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 2.) r.t., 1 h 4: NaBH4 / ethanol / 3 h / Heating View Scheme