Table 1 Optimization of reaction conditionsa
Entry | Copper salt (x mol%) | Catalyst (y mol%) | Solvent | Ligand | Yield (%)b | Drc | ee (%)c |
---|---|---|---|---|---|---|---|
1 | – | Cat-1 (10) | DCM | – | 32 | 95:5 | 2 |
2 | – | Cat-2 (10) | DCM | – | 49 | 90:10 | 7 |
3 | – | Cat-3 (10) | DCM | – | 50 | 95:5 | 3 |
4 | CuTC (10) | Cat-1 (10) | DCM | – | 53 | 84:16 | 4 |
5 | CuTC (10) | Cat-2 (10) | DCM | – | 60 | 69:31 | 64 |
6 | CuTC (10) | Cat-3 (10) | DCM | – | 70 | 66:34 | 87 |
7 | CuTC (10) | Cat-4 (10) | DCM | – | 64 | 90:10 | <5 |
8 | CuTC (10) | Cat-5 (10) | DCM | – | 31 | 80:20 | <5 |
9 | CuTC (10) | Cat-6 (10) | DCM | – | 67 | 67:33 | 71 |
10 | CuTC (10) | Cat-7 (10) | DCM | – | 50 | 95:5 | <5 |
11 | CuI (10) | Cat-3 (10) | DCM | – | 54 | 86:14 | 71 |
12 | Cu2O (10) | Cat-3 (10) | DCM | – | 36 | 95:5 | 54 |
13 | Cu(MeCN)4PF6 (10) | Cat-3 (10) | DCM | – | 52 | 70:30 | 16 |
14 | CuTC (10) | Cat-3 (10) | THF | – | 67 | 66:34 | 85 |
15 | CuTC (10) | Cat-3 (10) | Toluene | – | 45 | 87:13 | 23 |
16 | CuTC (10) | Cat-3 (10) | DCE | – | 40 | 75:25 | 22 |
17 | CuTC (10) | Cat-3 (10) | CH3CN | – | 70 | 60:40 | 79 |
18 | CuTC (10) | Cat-3 (10) | acetone | – | 64 | 67:33 | 85 |
19 | CuTC (10) | Cat-3 (10) | PhCl | – | 45 | 66:34 | 75 |
20 | CuTC (10) | Cat-3 (10) | 1,4-dioxane | – | 71 | 66:34 | 83 |
21d | CuTC (10) | Cat-3 (10) | DCM | – | 70 | 60:40 | 90 |
22d, e | CuTC (10) | Cat-3 (10) | DCM | – | 40 | 70:30 | 92 |
23d | CuTC (10) | – | DCM | L1 | 29 | 80:20 | 15 |
24d | CuTC (10) | Cat-3 (10) | DCM | L1 | 40 | 60:40 | 42 |
25d | CuTC (10) | Cat-3 (10) | DCM | L2 | 43 | 75:25 | 4 |
26d | CuTC (10) | Cat-3 (10) | DCM | L3 | 56 | 75:25 | 17 |
27d | CuTC (10) | Cat-3 (20) | DCM | – | 72 | 80:20 | 93 |
28d, e | CuI (15) | Cat-3 (30) | DCM | – | 62 | 78:22 | 79 |
29d, e | CuTC (15) | Cat-3 (30) | DCM | – | 72 | 70:30 | 90 |
30d, e | CuTC (10) | Cat-3 (25) | DCM | – | 71 | 90:10 | 94 |
31d, e | CuTC (10) | Cat-3 (30) | DCM | – | 70 | 92:8 | 85 |