copper(I) thiophene-2-carboxylate; oxygen; triphenylphosphine; 2,2,2-trimethylacetic acid in dimethyl sulfoxide T=130°C; P=760.051 Torr; 23 h;

[2,2']bipyridinyl; copper(l) iodide; oxygen in N,N-dimethyl acetamide T=140°C; 18 h; Sealed tube;

sodium sulfate; scandium tris(trifluoromethanesulfonate) in N,N-dimethyl-formamide T=100°C; 20 h; Schlenk techniqueInert atmosphereGreen chemistry;

1.1: copper diacetate; sodium acetate / water / |Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / |Cooling with ice 2.2: 2 h / 80 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 5.1: scandium tris(trifluoromethanesulfonate); sodium sulfate / N,N-dimethyl-formamide / 20 h / 100 °C / |Schlenk technique; |Inert atmosphere; |Green chemistry View Scheme

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 2: scandium tris(trifluoromethanesulfonate); sodium sulfate / N,N-dimethyl-formamide / 20 h / 100 °C / |Schlenk technique; |Inert atmosphere; |Green chemistry View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 3: scandium tris(trifluoromethanesulfonate); sodium sulfate / N,N-dimethyl-formamide / 20 h / 100 °C / |Schlenk technique; |Inert atmosphere; |Green chemistry View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / |Cooling with ice 1.2: 2 h / 80 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 4.1: scandium tris(trifluoromethanesulfonate); sodium sulfate / N,N-dimethyl-formamide / 20 h / 100 °C / |Schlenk technique; |Inert atmosphere; |Green chemistry View Scheme

1.1: copper diacetate; sodium acetate / water / |Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / |Cooling with ice 2.2: 2 h / 80 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 100 °C 5.1: scandium tris(trifluoromethanesulfonate); sodium sulfate / N,N-dimethyl-formamide / 20 h / 100 °C / |Schlenk technique; |Inert atmosphere; |Green chemistry View Scheme

[2,2']bipyridinyl; copper(l) iodide; oxygen in N,N-dimethyl acetamide T=140°C; 24 h; Sealed tube; Overall yield = 96 percent;

1: diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.)-60 deg C, 5 h 2: DDQ / CH2Cl2 / 1 h View Scheme