Table 1. Optimization of the Reaction Conditionsa.
| entry | variations from standard conditions | yieldb |
|---|---|---|
| 1 | None | 88% |
| 2 | No FeCl3 | N.Dc |
| 3 | No HOAc | N.Dc |
| 4 | FeCl2 instead of FeCl3 | 71% |
| 5 | FeBr3 instead of FeCl3 | 81% |
| 6 | Fe(acac)3 instead of FeCl3 | 11% |
| 7 | Fe(NO3)3 instead of FeCl3 | 7% |
| 8 | CuBr instead of FeCl3 | 6% |
| 9 | AgOAc instead of FeCl3 | 10% |
| 10 | 10 mol % of FeCl3 | 72% |
Reaction conditions: 1a (0.2 mmol), 2a (2.0 equiv), FeCl3 (20 mol %), HOAc (10.0 equiv), and EtOAc (2.0 mL) at r.t. under Ar for 8 h. The d.r. of 3a was about 9:1.
Isolated yields.
N.D. = Not detected.
