1: 100 percent / toluene / 1) 1h ambient temperature 2) 1h reflux 2: 12 percent / m-chloroperoxybenzoic acid / CH2Cl2 / Heating 3: 1) N-bromsuccinimide 2) 1,5-diazabicyclo<5.4.0>undec-5-en (DBU) / 1) dibenzoylperoxide, CCl4, 60 min reflux 2) THF, a) cooling with CO2 (s)/CCl4, b) ambient temperature (24h) 4: 11.6 percent / anhydrous hydrazine / CH2Cl2 / 24 h / Ambient temperature 5: tetradeuteriomethanol View Scheme

NaOAc buffer; oxygen; copper(II) sulfate T=37°C; 1 h; dopamine β-monooxygenase; Rate constant;

dopamine β-monooxygenase O2, ascorbate; kcat; Rate constantMechanism;

1: 100 percent / toluene / 1) 1h ambient temperature 2) 1h reflux 2: 53 percent / m-chloroperoxybenzoic acid / CH2Cl2 / Heating 3: 76 percent / bromine / CH2Cl2 / 2.5 h / -78 °C 4: 94 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 24 h / 1) ice bath 2) room temperature 5: 51 percent / anhydrous hydrazine / CH2Cl2 / 24 h / Ambient temperature 6: 92 percent / NaN3 / various solvent(s) / 0.75 h View Scheme

1: 100 percent / toluene / 1) 1h ambient temperature 2) 1h reflux 2: 12 percent / m-chloroperoxybenzoic acid / CH2Cl2 / Heating 3: 1) N-bromsuccinimide 2) 1,5-diazabicyclo<5.4.0>undec-5-en (DBU) / 1) dibenzoylperoxide, CCl4, 60 min reflux 2) THF, a) cooling with CO2 (s)/CCl4, b) ambient temperature (24h) 4: over silica gel View Scheme