Table 1. Screening of Metal Catalysts and Silyl Reagents.
entry | catalyst | silyl | silyl-OTf (equiv) | react time (min) | conva (%) |
---|---|---|---|---|---|
1 | Cu(OTf)2 | Me3Si | 1.0 | 60 | 75 |
2 | Cu(OTf)2 | Me3Si | 1.5 | 50 | 90 |
3 | CuI | Me3Si | 1.0 | 60 | 53 |
4 | CuI | Me3Si | 1.5 | 50 | 67 |
5 | CuOTf | Me3Si | 1.0 | 60 | 74 |
6 | CuOTf | Me3Si | 1.5 | 50 | 76 |
7 | Sc(OTf)3 | Me3Si | 1.5 | 50 | 43 |
8 | Rh[COD]2Cl2 | Me3Si | 1.5 | 20 | 68 |
9 | Zn(OTf)2 | Me3Si | 1.5 | 20 | 91 |
10 | Zn(OTf)2 | Et3Si | 1.5 | 210 | 76 |
11 | Zn(OTf)2 | iPr3Si | 1.5 | 600 | 64 |
12 | Zn(OTf)2 | tBu2PhSi | 1.5 | 1440 | 53b |
Determined by 1H NMR.
Reaction incomplete after 24 h.