Table 3.
Influence of the phosphine oxide ligands on the catalyst performance in the N-oxidation of 1a
| Entry | Ligand | TON |
|---|---|---|
| 1b | H3PO4 | 11 |
| 2 | Ph3PO | 12 |
| 3 | (p-FC6H4)3PO | 14.6 |
| 4 | [3,5-(CF3)2C6H3]3PO | 6.9 |
| 5 | Me2PhPO | 7.5 |
| 6 | tBuPh2PO | 8.9 |
| 7 | (o-Tol)3PO | 1.8 |
| 8 | o-C6H4(PPh2O)2 | 1 |
| 9 | Et3PO | 12.9 |
| 10 | (Me2N)3PO | 8.1 |
| 11c | dppe-dioxide | 3.9 |
| 12c | dppm-dioxide | 2.2 |
| 13c | binap-dioxide | 2.1 |
Reaction conditions: 1 (1.4 mmol), MoO3 (5 mol%), ligand (5 mol%) CH3CN (1 mL), H2O2 (30% aq. solution, 4 equiv.), 50 °C, 4 h.
1.25 mol% H3PO4 was used.
dppe = 1,2-bis(diphenylphosphino)-ethane, dppm = bis(diphenylphosphino)methane, binap = 2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl.