Optimization for the formation of 3.
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Entry | Variation from standard conditionsa | Yieldb [%] |
1 | None | 96 |
2 | W/o Cu(OTf)2 | No reaction |
3 | Cu(OTf)2 (1 mol%) | 65 |
4 | Cu(OTf)2 (5 mol%) | 99 |
5 | Cu(OTf)2 (8 mol%) | 99 |
6 | Ni(OTf)2 instead of Cu(OTf)2 | 61 |
7 | Zn(OTf)2 instead of Cu(OTf)2 | 15 |
8 | Sc(OTf)2 instead of Cu(OTf)2 | 44 |
9 | DCE instead of DCM | 91 |
10 | 0 °C | 34 |
11 | 50 °C | 98 |
12 | 80 °C | 75 |
13 | 1 (0.60 mmol) | 84 |
14 | 2 (1.5 equiv.) | 99 |
Standard conditions: 1 (1.2 equiv.), 2 (0.30 mmol, 1.0 equiv.), Cu(OTf)2 (3 mol%), DCM (1.0 mL), 25 °C, 12 h.
Isolated yield (average of 2 independent runs). DCE = 1,2-dichloroethane, DCM = dichloromethane.