. 2019 Mar 13;9(15):8197–8203. doi: 10.1039/c9ra01590f

Optimization of the hydroamination step of the consecutive process. Conditions for homocoupling: 1 equiv. 4-ethynyltoluene (c = 0.075 M), 6 mol% CuBr₂ as catalyst, DMSO as solvent, 120 °C, 35 min residence time. Conditions for hydroamination: 3 equiv. hydrazine (c = 0.1125 M), DMSO as solvent.

Entry	Temperature (°C)	Residence time (min)	Yield^a (%)
1	120	70	76
2	120	87.5	86
3	140	87.5	98

NMR yield, determined by ¹H NMR spectroscopy of the crude material. No traces of unreacted alkyne were found in the crude material.

Optimization of the hydroamination step of the consecutive process. Conditions for homocoupling: 1 equiv. 4-ethynyltoluene (c = 0.075 M), 6 mol% CuBr2 as catalyst, DMSO as solvent, 120 °C, 35 min residence time. Conditions for hydroamination: 3 equiv. hydrazine (c = 0.1125 M), DMSO as solvent.