Table 1 Optimization of the reaction conditionsa
Entry | Catalyst | Oxidant | Additive (x equiv) | Yield of 3a (%) | Yield of 4a (%) |
|---|---|---|---|---|---|
1 | [Co-1] | TBPB | / | 8 | 10 |
2 | [Co-1] | TBPB | K3PO4 (0.5) | 50 | 18 |
3 | [Co-1] | TBPB | K2CO3 (0.5) | 32 | 20 |
4 | [Co-1] | TBPB | t-BuOK (0.5) | 36 | 14 |
5 | [Co-1] | DTPB | K3PO4 (0.5) | 26 | 15 |
6 | [Co-1] | BPO | K3PO4 (0.5) | 26 | Trace |
7 | [Co-1] | m-CPBA | K3PO4 (0.5) | Trace | Trace |
8 | [Co-1] | TBPB | Mn(OAc)2 (1.0) | 70 | 30 |
9 | [Co-2] | TBPB | Mn(OAc)2 (1.0) | 60 | 8 |
10 | [Co-2] | TBPB | Mn(OAc)2‧4H2O (1.0) | 70 | 10 |
11b | [Co-2] | TBPB | Mn(OAc)2‧4H2O (0.6) | 95% (89%)c | Trace |
12 | / | / | AgTFA (2.0) | N.D. | 48 |
13 | / | / | AgOAc (2.0) | N.D. | N.D. |
14 | / | / | AgF (2.0) | N.D. | 34 |
15 | / | / | KF (2.0) | N.D. | N.D. |
16 | / | / | CsF (2.0) | N.D. | N.D. |
17 | / | / | Ae | N.D. | 99% (94%)c |
18 d | / | / | Ae | N.D. | 84 |
19 d | / | / | Bf | N.D. | 60 |
20 d | / | / | Cg | N.D. | 38 |

