Condition for one pot domino C–C/C–O arylations reaction 1,2,3-triiodobenzene 5 with 1,2-bis(4-methoxy phenyl)ethane-1-onea.
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| Entry | Catalyst (mol%) | Ligand (mol%) | Base (equiv.) | Solvent [M] | T (°C) | Yield of 7ab (%) |
| 1 | Pd(OAc)2 (10) | PPh3 (20) | NA | DMF, [0.2] | 120 | 18% |
| 2 | Pd(OAc)2 (10) | PPh3 (20) | NA | Toluene, [0.2] | 120 | 27% |
| 3 | Pd(OAc)2 (10) | PPh3 (30) | NA | Toluene, [0.2] | 120 | 29% |
| 4 | Pd(OAc)2 (20) | PPh3 (30) | NA | Toluene, [0.2] | 120 | 32% |
| 5 | Pd(OAc)2 (20) | PPh3 (30) | NA | Toluene, [0.15] | 120 | 34% |
| 6 | Pd(OAc)2 (20) | PPh3 (30) | NA | Toluene, [0.1] | 120 | 39% |
| 7 | Pd(OAc)2 (20) | PPh3 (30) | Cs2CO3 (2) | Toluene, [0.1] | 120 | 37% |
| 8 | Pd(OAc)2 (20) | PPh3 (30) | Cs2CO3 (3) | Toluene, [0.1] | 120 | 35% |
| 9 | Pd(PPh3)4 (20) | NA | NA | Toluene, [0.1] | 120 | 37% |
| 10 | Pd(PPh3)4 (20) | NA | Cs2CO3 (2) | Toluene, [0.1] | 120 | 54% |
| 11 | Pd(PPh3)4 (20) | NA | Cs2CO3 (3) | Toluene, [0.1] | 120 | 64% |
| 12 | Pd(PPh3)4 (20) | NA | Cs2CO3 (4) | Toluene, [0.1] | 120 | 65% |
| 13 | Pd(PPh 3 ) 4 (20) | NA | Cs 2 CO 3 (3) | Toluene, [0.1] | 130 | 75% |
| 14 | Pd(PPh3)4 (20) | NA | Cs2CO3 (3) | Toluene, [0.2] | 130 | 61% |
| 15 | Pd(PPh3)4 (20) | NA | K2CO3 (3) | Toluene, [0.1] | 130 | 59% |
| 16 | Pd(PPh3)4 (20) | NA | Cs2CO3 (3) | O-Xylene, [0.1] | 130 | 51% |
| 17c | Pd(PPh3)4 (20) | NA | Cs2CO3 (3) | Toluene, [0.1] | 130 | 29% |
| 18d | Pd(PPh3)4 (20) | NA | Cs2CO3 (3) | Toluene, [0.1] | 130 | 67% |
a
Conditions: All reactions were carried out using 0.65 mmol (1.0 equiv., 0.1 M) of 1,2,3-triiodobenzene 5 in 6.5 solvent.
b
Isolated yields.
c
Reflux was used.
d
1.0 gram scale (2.19 mmol).