Table 5.
The Pd(OAc)2-catalyzed carbonylation of tetraphenylene (1).
 | |||||
| Entry | PhCN (equiv) | Pd(OAc)2 (equiv) | DMSO (equiv) | Additive (0.2 mL) | Yielda (%) |
| 1 | 2.0 | 10% | 1.0 | / | 20 |
| 2 | 2.0 | 10% | 2.0 | / | 42 |
| 3 | 2.0 | 10% | 4.0 | / | 28 |
| 4 | 2.0 | 10% | 2.0 | DCM | 52 |
| 5 | 2.0 | 10% | 2.0 | DCE | 36 |
| 6 | 2.0 | 20% | 2.0 | DCM | 71 |
| 7 | 2.0 | 20% | 2.0 | DCM | 60b |
| 8 | 2.0 | 20% | 2.0 | DCM | 64c |
| 9 | 2.5 | 20% | 2.0 | DCM | 83 (80)d |
| 10 | 3.0 | 20% | 2.0 | DCM | 60 |
aThe yields were determined by 1H NMR analysis of the crude products using CH2Br2 as the internal standard. bReaction temperature 90 °C. cReaction temperature 110 °C. dIsolated yields based on tetraphenylene (1).