Table 1. Optimisation of the cross-coupling of thiocarbonylthio 5 with boronic acid 4b.
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Entry 5 |
Cu salt | Solvent | Temp | Yield a | |
1 | a | Cu(acac) | THF | 66 | 0 |
2 | ′′ | CuCl2·H2O | ′′ | ′′ | Trace |
3 | ′′ | Cu powder | ′′ | ′′ | 12 |
4 | ′′ | Cu(OAc)2·H2O | ′′ | ′′ | 21 |
5 | ′′ | Cu(BF4)2·H2O | ′′ | ′′ | 35 |
6 | ′′ | ′′ | Dioxane | ′′ | 12 |
7 | ′′ | ′′ | DMF | ′′ | 21 |
8 | ′′ | ′′ | Toluene | ′′ | 16 |
9 | ′′ | ′′ | CH2Cl2 | 40 | 42 |
10 | ′′ | ′′ | DCE | 66 | 54 |
11 a | b | ′′ | DCE | 80 | 67 |
12 a | b | Cu(BF4)2·H2O·EtOAc | ′′ | 80 | 85 |
aIsolated yields.