hydrogenchloride; 2-methylpropylboronic acid in methanol; n-heptane; water T=25 - 30°C; 1 - 2 h; Product distribution / selectivity;

hydrogenchloride in methanol; pentane 20 h;

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine in not given 1. (2-pyrazine)CO2H, TBTU, i-Pr2EtN, 0°C - room temp.; 2. i-BuB(OH)2, pentane, MeOH, 1 N HCl;

1: N-ethyl-N,N-diisopropylamine / dichloromethane 2: methanol / |Acidic conditions View Scheme

1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane 2: hydrogen; palladium 10 on activated carbon / N,N-dimethyl-formamide 3: N-ethyl-N,N-diisopropylamine / dichloromethane 4: methanol / |Acidic conditions View Scheme

1: di-isopropyl ether / 2 h / -10 - 0 °C / |Large scale 2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / |Large scale 3: hydrogenchloride / toluene / 1 h / 0 °C / |Large scale 4: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C / |Large scale 5: hydrogenchloride; 2-methylpropylboronic acid / hexane; MeOD-d4; water / 0 - 20 °C / |Large scale View Scheme

1.1: dichloromethane / 0.08 h / 0 °C / |Inert atmosphere 1.2: 1 h / -3 - 2 °C 1.3: 0.25 h / 15 - 27 °C 2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / toluene / 0.17 h / |Inert atmosphere 2.2: 3 h / 25 °C 3.1: hydrogenchloride; 2-methylpropylboronic acid / methanol; n-heptane / 12 h / 20 °C View Scheme

hydrogenchloride; oxygen in dimethyl sulfoxide T=70°C; Oxidation; hydrolysis; pH=1.0; 250 h; KineticsProduct distribution;

sodium hydroxide; oxygen in dimethyl sulfoxide T=70°C; Oxidation; hydrolysis; pH=12.0; 250 h; KineticsProduct distribution;

dihydrogen peroxide in water T=20°C; Oxidation; hydrolysis; 1 h; KineticsProduct distribution; Further Variations:Solvents;