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. Author manuscript; available in PMC: 2008 Aug 20.
Published in final edited form as: J Org Chem. 2006 Oct 27;71(22):8680–8683. doi: 10.1021/jo061688m

Table 1.

Preparation of 1,4,5-Trisubstituted-1,2,3-triazoles via Ru-Catalyzed Cycloadditions of Azides with Internal Alkynes

graphic file with name nihms-61506-t0005.jpg
entry R1 R2 R3 equiv. alkyne time (h) % yield ratio A:B
1 Ph Me CH2Ph 2.0 2.5 95 38:62
2 Ph Pr CH2Ph 1.5 2.5 80 13:87
3 Ph CO2Et CH2Ph 2.0 2.5 85 100:0
4 Ph COMe CH2Ph 1.5 2.5 100 100:0
5 Ph CH2OH CH2Ph 1.5 5.0 70 0:100
6 Ph CH(OEt)2 CH2Ph 1.5 2.5 75 50:50
7 Me Pr CH2Ph 3.0 16 75 32:68
8 Et Et CH2Ph 2.0 6.0 85 N/A
9 Me t-Bu CH2Ph 5.0 36 15 0:100
10 Me CH2CH2OH CH2Ph 1.5 8.0 90 33:77
11 Bu CO2Me CH2Ph 1.2 2.5 90 100:0
12 Et COMe CH2Ph 1.5 2.5 90 100:0
13 Me CH2NEt2 CH2Ph 1.5 2.5 70 0:100
14 Et CMe2OH CH2Ph 1.5 5.0 80 0:100
15 Ph Me CHPh2 3.0 20 65 33:67
16 Ph Me 1-adamantyl 5.0 40 10 0:100