From: Palladium-catalyzed borylation of aryl (pseudo)halides and its applications in biaryl synthesis
Entry | Catalyst | Solvent | Base | Temp. (°C) | Time (h) | Yielda (%) |
---|---|---|---|---|---|---|
1 | Pd(PPh3) b4 | DMSO | KOAc | 80 | 8 | Tracec |
2 | Pd(PPh3)4/PCy b3 | Dioxane | KOAc | 80 | 8 | 72c |
3 | PdCl2(PPh3) b2 | DMF | K3PO4 | 80 | 8 | 12c |
4 | PdCl2(dppf)b | DMF | K3PO4 | 80 | 8 | Tracec |
5 | PdCl2(dppf)b | DMSO | KOAc | 80 | 8 | Tracec |
6 | Pd2dba3/PCy b3 | Dioxane | KOAc | 110 | 8 | 67c |
7 | Pd2dba3/XPhosb | Dioxane | KOAc | 110 | 8 | 81c |
8 | Pd2dba3/SPhosb | Dioxane | KOAc | 110 | 8 | 48c |
9 | Pd(OAc)2/PCy b3 | Dioxane | KOAc | 110 | 2 | 69c |
10 | Pd(OAc)2/XPhosb | Dioxane | KOAc | 110 | 2 | 76c |
11 | Pd(OAc)2/SPhos | Dioxane | KOAc | RT | 48 | 42 |
12 | 9a | THF | KOAc | RT | 2 | Traced |
13 | 9a | EtOH | KOAc | RT | 2 | 13d |
14 | 9b | THF | KOAc | RT | 2 | 23d |
15 | 9b | EtOH | KOAc | RT | 2 | 66d |
16 | 10a | THF | KOAc | RT | 2 | 21d |
17 | 10a | EtOH | KOAc | RT | 2 | 12d |
18 | 10b | THF | KOAc | RT | 2 | 93d |
19 | 10b | EtOH | KOAc | RT | 2 | 35 |
20 | 10b | THF | K3PO4 | RT | 1 | 87e, 98f |