Table 1.
Entry a) | Catalyst | Yield (%) b) | Ratio of 4a:4a’ c) |
---|---|---|---|
1 | CuCl@POL‐NHC‐Et | 74 | 93:7 |
2 | CuCl@POL‐NHC‐Cy | 80 | 99:1 |
3 | CuCl@POL‐NHC‐Ph | 88 | >99:1 |
4 | CuCl@POL‐NHC‐BI | 70 | 94:6 |
5 | Cu(OTf)2@POL‐NHC‐Ph | 38 | 96:4 |
6 | CuCl2@POL‐NHC‐Ph | 48 | >99:1 |
7 | CuBr@POL‐NHC‐Ph | trace | – |
8 d) | CuCl‐NHC‐Ph | trace | – |
9 | CuCl@POL‐NHC‐PI | 75 | >95:5 |
10 | POL‐NHC‐Ph | 0 | – |
Reaction conditions: 1a (0.5 mmol), 2a (2 equiv), 3a (1.5 equiv), NaO t Bu (1.5 equiv), [Cu]@POL‐NHC (20 mg), DMF (0.25 M), 60°C, 7 h;
Isolated yield;
Determined by using 1H NMR spectroscopy;
4 mol% CuCl‐NHC‐Ph. The conversion rate of NHC in [Cu]@POL‐NHC is shown in Table S4 (Supporting Information).