Table 1 Optimization of the reaction conditions
Entry | Cat. (10 mol%) | Ligand (x equiv.) | Base (y equiv.) | Solvent | Yield(%)a | |||
---|---|---|---|---|---|---|---|---|
3 | 4 | 5 | ||||||
1 | CuSCN | Phen (0.1) | MeOLi (1) | THF | 82 (75)b | 5 | 4 | |
2c | CuSCN | Phen (0.1) | MeOLi (1) | THF | 74 | 2 | 7 | |
3 | CuI | Phen (0.1) | MeOLi (1) | THF | 33 | 3 | 8 | |
4 | CuCl | Phen (0.1) | MeOLi (1) | THF | 52 | 2 | 8 | |
5 | CuSCN | Bphen (0.1) | MeOLi (1) | THF | 71 | 8 | 6 | |
6 | CuSCN | PPh3 (0.1) | MeOLi (1) | THF | 65 | 7 | 3 | |
7 | CuSCN | PCy3 (0.1) | MeOLi (1) | THF | 16 | 10 | 2 | |
8 | CuSCN | P(o-tol)3 (0.1) | MeOLi (1) | THF | 37 | 6 | 1 | |
9 | CuSCN | Phen (0.1) | t-BuOK (1) | THF | 8 | 31 | 15 | |
10 | CuSCN | Phen (0.1) | DBU (1) | THF | 1 | 27 | 18 | |
11 | CuSCN | Phen (0.1) | MeOLi (2) | THF | 38 | 43 | 12 | |
12 | CuSCN | Phen (1.0) | MeOLi (2) | THF | 35 | 55 | 1 | |
13 | CuSCN | Phen (1.0) | MeOLi (2) | CH3CN | trace | 59 | 34 | |
14d | CuSCN | Phen (1.0) | MeOLi (2) | CH3CN | trace | 93 (71)b | 1 | |
15d,e | CuIf | Phen (1.0) | t-BuOK (1.5) | DCM | trace | trace | 90 (80)b |