Table 1 Optimization of reaction conditionsa
Entry | Ni Cat. | Ligand | Reductant | Solvent | Yield of 4 (%) | Recovery of 1a (%) |
|---|---|---|---|---|---|---|
1 | NiBr2•DME | L1 | Zn | DMA | 0 | 77 |
2 | NiBr2•DME | L2 | Zn | DMA | 0 | 87 |
3 | NiBr2•DME | L3 | Zn | DMA | 6 | 73 |
4 | NiBr2•DME | L4 | Zn | DMA | 30 | 52 |
5 | NiBr2•DME | L5 | Zn | DMA | 0 | 97 |
6 | NiBr2•DME | L6 | Zn | DMA | 14 | 79 |
7 | Ni(acac)2 | L4 | Zn | DMA | 15 | 83 |
8 | Ni(OTf)2 | L4 | Zn | DMA | 25 | 55 |
9 | Ni(COD)2 | L4 | Zn | DMA | 12 | 54 |
10 | Ni(PPh3)2Cl2 | L4 | Zn | DMA | 35 | 47 |
11 | Ni(PPh3)2Cl2 | L4 | Zn | DMSO | 0 | 70 |
12 | Ni(PPh3)2Cl2 | L4 | Zn | CH3CN | 0 | 94 |
13 | Ni(PPh3)2Cl2 | L4 | Zn | EtOAc | 0 | 88 |
14b | Ni(PPh3)2Cl2 | L4 | Zn | DMA | 60 | 21 |
15b,c | Ni(PPh3)2Cl2 | L4 | Zn | DMA | 55 | 63 |
16b | Ni(PPh3)2Cl2 | L4 | Mn | DMA | 4 | 64 |
17b | Ni(PPh3)2Cl2 | L4 | TDAE | DMA | trace | 72 |
18b,d | Ni(PPh3)2Cl2 | L4 | Zn | DMA | 79 (73e, 55f) | 0 |
