Table 3.
Entry | Substrate | Product | Yield (%)b |
1 |
1 |
2 |
82 |
2 |
3a |
2 |
80 |
3 |
3b |
4b |
–c |
4 |
3c |
4c |
96 |
5 |
3d |
4d |
88d |
6 |
3e |
4e |
83 |
7 |
3f |
4f |
96 |
8 |
3g |
4g |
96 |
9 |
3h |
4h |
75 |
10 |
3i |
4i |
99 |
aReactions were performed on a 1 mmol scale in 1 mL of methanol at 70 °C for 20 h. 15 min prior to workup, the mixture was quenched by addition of 1,2-dibromoethane (20 μL, 0.23 equiv). bYields of pure isolated material. cNo reaction to coumarin observed; starting material (60%) was reisolated. dReaction performed at 90 °C in a closed vessel.