Optimization of reaction conditionsa.
| |||||
|---|---|---|---|---|---|
| Entry | Catalyst | Oxident (R) | Yieldb (%) | ||
| 4a | 4aa | 4ab | |||
| 1 | PPh3AuNTf2 | 3a (2,6-Br2) | <1 | 90 | <1 |
| 2 | IPrAuNTf2 | 3a (2,6-Br2) | 17 | 72 | <1 |
| 3 | Zn(OTf)2 | 3a (2,6-Br2) | 75 | <1 | 12 |
| 4 | Fe(OTf)3 | 3a (2,6-Br2) | 65 | <1 | 32 |
| 5 | Yb(OTf)3 | 3a (2,6-Br2) | 69 | <1 | 12 |
| 6 | In(OTf)3 | 3a (2,6-Br2) | 64 | <1 | 18 |
| 7 | Sm(OTf)3 | 3a (2,6-Br2) | 74 | <1 | <1 |
| 8 | Sc(OTf) 3 | 3a(2,6-Br2) | 95 | <1 | <1 |
| 9 | HNTf2 | 3a (2,6-Br2) | 39 | <1 | 23 |
| 10 | MsOH | 3a (2,6-Br2) | <1 | <1 | 70 |
| 11 | Sc(OTf)3 | 3b (2,6-Cl2) | 88 | <1 | 6 |
| 12 | Sc(OTf)3 | 3c (2-Br) | 80 | <1 | 11 |
Reactions run in vials; [1a] = 0.05 M.
Estimated by 1H NMR using diethyl phthalate as an internal reference.