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. 2016 May 17;3(11):1600048. doi: 10.1002/advs.201600048

Table 1.

Cycloaddition reaction of CO2 with 1‐ethyl‐2‐phenylaziridine under various conditionsa)

graphic file with name ADVS-3-0g-g005.jpg
Entry Catalyst 1 [mg] T [°C] Yieldb) [%] Regio‐selc)
1 80 25 30 97:3
2 80 80 91 97:3
3 80 100 >99 98:2
4 80 120 85 97:3
5d) 80 100 92 98:2
6 40 100 89 98:2
7e) 0 100 45 92:8
8f) 0 100 43 92:8
9g) 0 100 47 >99
10 0 100 79 98:2
11h) 40 100 95 96:4

a)Reaction conditions: 1‐ethyl‐2‐phenylaziridine (294.4 mg, 2.0 mmol), solvent‐free, catalyst 1, TBAB (32.4 mg, 0.1 mmol), CO2 (2.0 MPa), 12 h, 80 mg catalyst 1 loading (based on metal center, about 10 mol%);

b)Total yield of 2a and 3a determined by 1H NMR using 1,3,5‐trimethoxybenzene as an internal standard;

c)Molar ratio of 2a to 3a;

d)CO2 (1.0 MPa);

e)TBAB (32.4 mg, 0.1 mmol) and Cu(OAc)2 (39.9 mg, 0.2 mmol);

f)TBAB (32.4 mg, 0.1 mmol) and Cu(NO3)2 (37.4 mg, 0.2 mmol);

g)TBAB (32.4 mg, 0.1 mmol) and CuSO4 (31.9 mg, 0.2 mmol);

h)HKUST replaces compound 1 to conduct this reaction, catalyst loading (based on metal center, about 10 mol%).