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. 2020 Jan 21;10(6):3407–3415. doi: 10.1039/c9ra10171c

Synthesis of Cu-MOF-catalysed 1,4-disubstituted-1,2,3-triazole derivativesa.

graphic file with name c9ra10171c-u6.jpg
Entry R1 R2 Product [Cu(INA)2(H2O)4]-complex Cu(INA)2-MOF
Time Yieldb (%) Time (h) Yieldb (%)
1 PhCH2, 1a Ph, 2a graphic file with name c9ra10171c-u7.jpg 12 min 93 4 min 95
2 1a 4-OMeC6H4, 2b graphic file with name c9ra10171c-u8.jpg 5 min 85 4 min 90
3 1a 4-MeC6H4, 2c graphic file with name c9ra10171c-u9.jpg 6 min 81 5 min 90
4 1a 1-Naphthyl, 2d graphic file with name c9ra10171c-u10.jpg 1 h 97 1 h 95
5 1a 4-NH2C6H4, 2e graphic file with name c9ra10171c-u11.jpg 10 min 70 10 min 96
6 4-OMeC6H4, 1b 2a graphic file with name c9ra10171c-u12.jpg 10 min 86 10 min 92
7 1b 2e graphic file with name c9ra10171c-u13.jpg 40 min 70 40 min 90
8 1b 2c graphic file with name c9ra10171c-u14.jpg 1 h 95
9 1a PhCH2Se, 2f graphic file with name c9ra10171c-u15.jpg 2 h 80 2 h 86
10 1a PhSe, 2g graphic file with name c9ra10171c-u16.jpg 1.5 h 96c 1.5 h 98
11 1a PhSeCH2, 2h graphic file with name c9ra10171c-u17.jpg 12 h 50 12 h 70
a

Reaction conditions: azide (0.5 mmol), acetylene (0.5 mmol), catalyst (1 mol%).

b

Isolated yield.

c

A mixture of 1 : 1.4 ratio of the 1,4- and 1,5-regioisomers determined by 1H NMR spectroscopy.