Table 2.

Optimization of hydroazidation with ADC gold(I) catalysts

Entry[a]	Precatalyst	Solvent	Acid	Yield[b]	ee[c]
1	A1·(AuCl)2	THF	TFA	24	50
2	A2·(AuCl)2	THF	TFA	36	72
3	A3·(AuCl)2	THF	TFA	15	46
4	A4·(AuCl)2	THF	TFA	41	50
5	A5·(AuCl)2	THF	TFA	45	73
6	A5·(AuCl)2	THF	AcOH	40	71
7	A5·(AuCl)2	THF	H2O	77	75
8	A5·(AuCl)2	THF/PhMe[d]	H2O	91	73
9	A5·(AuCl)2	THF/CHCl3[d]	H2O	91	73
10[e]	A5·(AuCl)2	THF/CHCl3[d]	H2O	92	90[f]

^[a]Conditions: 0.1 mmol 3a, 0.005 mmol precatalyst, 0.015 mmol AgOTf, 0.3 mmol TMSN₃, 0.2 mmol acid, 2.0 mL of appropriate solvent (0.05 M), 16 h at room temperature.

^[b]Determined by ¹H NMR with 4-chloroanisole as an internal standard.

^[c]Determined by chiral HPLC.

^[d]3:1 volumetric ratio.

^[e]Reaction run at −10 °C for 72 hours.

^[f]Isolated yield.