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. 2020 Jul 17;5(29):18472–18483. doi: 10.1021/acsomega.0c02390

Table 2. Evaluation of the Ring-Closing Metathesis toward Goniothalamin (1) under Flow Conditions.

2.3.

entry R conc. (M) catalyst loading (mol %) T (°C) t (min) conv. (%)a 1/17/19 or 1/18/20a yield (1 + 19 or 1 + 20) (%)b
1 H 0.05 Grubbs I 10 100 16.0 23 100:0:0 NDc
2 H 0.01 Grubbs II 5 100 16.0 90 79:0:21 90
3 H 0.05 Grubbs II 5 50 16.0 100 38:44:18 55
4 H 0.05 Grubbs II 5 100 16.0 100 57:0:43 78
5 H 0.05 Grubbs II 1 100 16.0 55 83:0:17 NDc
6 H 0.05 Grubbs II 5 100 8.0 97 54:0:46 79
7 H 0.01 Hoveyda II 5 100 16.0 100 44:0:56 97
8 H 0.05 Hoveyda II 5 100 16.0 100 41:0:59 58
9 Me 0.05 Grubbs I 10 100 16.0 0    
10 Me 0.01 Grubbs II 5 100 16.0 80 100:0:0 75 (1 only)
11 Me 0.01 Grubbs II 5 100 32.0 75 100:0:0 65 (1 only)
12 Me 0.05 Grubbs II 5 100 16.0 100 66:0:34 94
13 Me 0.01 Hoveyda II 5 100 16.0 100 83:0:17 91
14 Me 0.05 Hoveyda II 5 100 16.0 100 63:0:37 77
a

Calculated from 1H NMR of the crude.

b

Isolated yield for the inseparable mixture.

c

ND = not determined.