Alkyne-Azide Cycloaddition Catalyzed by Silver Chloride and “Abnormal” Silver N-Heterocyclic Carbene Complex

Table 1

Synthesis of triazole 3 catalyzed by silver salts.

Entry	Silver salt	Catalyst ratio (% mol)	Solvent	Reaction time (h)	% Yield
1	AgNO3	1	H2O	48	0
2	AgNO3	1	THF	48	8
3	Ag2SO4	1	H2O	48	0
4	Ag2SO4	1	THF	48	0
5	Ag2O	1	H2O	48	0
6	Ag2O	1	THF	48	0
7	AgCl	0.5	Acetone	24	35
8	AgCl	0.5	THF	24	27
9	AgCl	0.6	H2O	24	35
10	AgCl	0.6	Acetone	24	47
11	AgCl	0.6	H2O/acetone	24	55
12	AgCl	0.6	CH2Cl2	24	0
13	AgCl	0.6	CH3OH	24	31
14	AgCl	0.6	THF	24	25
15	AgCl	1	H2O/acetone	24	58
16	AgCl	3.5	H2O/acetone	24	64
17	AgCl	5	H2O/acetone	24	64