tributyl-amine; Pd(PPh3) in acetonitrile T=65°C; P=760 Torr; 15 h;

tributyl-amine; triphenylphosphine; palladium diacetate in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=100°C; 5 h;

1: 97 percent / 5percent KOH / methanol; H2O 2: NEt3 / tetrahydrofuran / 0.75 h / -10 °C 3: 59 percent / tetrahydrofuran / Ambient temperature 4: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 5: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C View Scheme

1: 67 percent / NaCl, H2O / dimethylsulfoxide / 8 h / Heating 2: 97 percent / 5percent KOH / methanol; H2O 3: NEt3 / tetrahydrofuran / 0.75 h / -10 °C 4: 59 percent / tetrahydrofuran / Ambient temperature 5: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 6: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C View Scheme

1: NEt3 / tetrahydrofuran / 0.75 h / -10 °C 2: 59 percent / tetrahydrofuran / Ambient temperature 3: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 4: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C View Scheme

1: 49 percent / NaBH4, acetic acid / tetrahydrofuran / 3.5 h / Heating 2: 61 percent / PPh3, n-Bu3N / Pd(OAc)2 / hexamethylphosphoric acid triamide / 5 h / 100 °C View Scheme

tributyl-amine; triphenylphosphine; palladium diacetate in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=120°C; 3 h; var. temp., var. times; Product distribution;

hydrogen; platinum(IV) oxide in ethanol