1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / benzene / 4 h / 20 °C View Scheme

1.1: methanol; pyridinium p-toluenesulfonate / 3 h / 0 - 20 °C / Inert atmosphere 2.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 3.2: 0 °C 4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: methanol; toluene-4-sulfonic acid / 6 h / 0 - 20 °C / Inert atmosphere 6.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 7.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 7.2: 0 - 20 °C / Inert atmosphere 7.3: 20 °C 8.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 9.1: palladium 10 on activated carbon; hydrogen / benzene / 4 h / 20 °C View Scheme

1.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 2.2: 0 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Reflux 3.2: 4 h / Inert atmosphere; Reflux 4.1: methanol; toluene-4-sulfonic acid / 6 h / 0 - 20 °C / Inert atmosphere 5.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 6.2: 0 - 20 °C / Inert atmosphere 6.3: 20 °C 7.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 8.1: palladium 10 on activated carbon; hydrogen / benzene / 4 h / 20 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 1.2: 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Reflux 2.2: 4 h / Inert atmosphere; Reflux 3.1: methanol; toluene-4-sulfonic acid / 6 h / 0 - 20 °C / Inert atmosphere 4.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 5.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 5.2: 0 - 20 °C / Inert atmosphere 5.3: 20 °C 6.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 7.1: palladium 10 on activated carbon; hydrogen / benzene / 4 h / 20 °C View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Reflux 1.2: 4 h / Inert atmosphere; Reflux 2.1: methanol; toluene-4-sulfonic acid / 6 h / 0 - 20 °C / Inert atmosphere 3.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 4.2: 0 - 20 °C / Inert atmosphere 4.3: 20 °C 5.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: palladium 10 on activated carbon; hydrogen / benzene / 4 h / 20 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux 1.2: 0 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 4.1: ammonia; lithium / tetrahydrofuran / 0.17 h / -33 °C / Inert atmosphere 5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere 5.2: 0.5 h / 0 °C / Inert atmosphere 5.3: 0 - 20 °C / Inert atmosphere 6.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene / 2 h / Inert atmosphere; Reflux 7.1: methanol; pyridinium p-toluenesulfonate / 3 h / 0 - 20 °C / Inert atmosphere 8.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 9.2: 0 °C 10.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Reflux 10.2: 4 h / Inert atmosphere; Reflux 11.1: methanol; toluene-4-sulfonic acid / 6 h / 0 - 20 °C / Inert atmosphere 12.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 13.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 13.2: 0 - 20 °C / Inert atmosphere 13.3: 20 °C 14.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 15.1: palladium 10 on activated carbon; hydrogen / benzene / 4 h / 20 °C View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 3.1: ammonia; lithium / tetrahydrofuran / 0.17 h / -33 °C / Inert atmosphere 4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere 4.2: 0.5 h / 0 °C / Inert atmosphere 4.3: 0 - 20 °C / Inert atmosphere 5.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene / 2 h / Inert atmosphere; Reflux 6.1: methanol; pyridinium p-toluenesulfonate / 3 h / 0 - 20 °C / Inert atmosphere 7.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux 8.2: 0 °C 9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Reflux 9.2: 4 h / Inert atmosphere; Reflux 10.1: methanol; toluene-4-sulfonic acid / 6 h / 0 - 20 °C / Inert atmosphere 11.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 12.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 12.2: 0 - 20 °C / Inert atmosphere 12.3: 20 °C 13.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 14.1: palladium 10 on activated carbon; hydrogen / benzene / 4 h / 20 °C View Scheme

in chloroform-d1

toluene-4-sulfonic acid in tetrahydrofuran; water T=50°C; 5 h; Yields of byproduct given;